Microtubule-stabilizing marine metabolite laulimalide and its derivatives: synthetic approaches and antitumor activity.

No abstract is available for this paper.

• Publication year

  2003

• Venue

  Chemical Reviews

• Publication date

  2003-08-14

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/CR940368CPMID 12964883
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• The solid state, solution and tubulin-bound conformations of agents that promote microtubule stabilization.

  2012cited by this paper
• Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues: the power of Sharpless' asymmetric epoxidation.

  2003cited by this paper
• Asymmetric total synthesis of (-)-laulimalide: exploiting the asymmetric glycolate alkylation reaction.

  2002cited by this paper
• Total synthesis of ionomycin using ring-opening strategies.

  2002cited by this paper
• A de novo enantioselective total synthesis of (-)-laulimalide.

  2002cited by this paper
• The microtubule stabilizing agent laulimalide does not bind in the taxoid site, kills cells resistant to paclitaxel and epothilones, and may not require its epoxide moiety for activity.

  2002cited by this paper
• Enantioenriched dihydropyrones from beta-lactone templates.

  2002cited by this paper
• Peloruside A, a novel antimitotic agent with paclitaxel-like microtubule- stabilizing activity.

  2002cited by this paper
• S(N)2 ring opening of beta-lactones: an alternative to catalytic asymmetric conjugate additions.

  2002cited by this paper
• Synthetic approaches to the microtubule stabilizing agent (-)-laulimalide.

  2002cited by this paper
• Lasonolide A: structural revision and synthesis of the unnatural (-)-enantiomer.

  2002cited by this paper
• Total synthesis of the microtubule-stabilizing agent (-)-laulimalide.

  2001cited by this paper
• Microtubule-stabilizing agents: a growing class of important anticancer drugs.

  2001cited by this paper
• Triple ring closing metathesis reaction: synthesis of adjacent cyclic ethers.

  2001cited by this paper
• The Spongistatins: Architecturally Complex Natural Products-Part One: A Formal Synthesis of (+)-Spongistatin 1 by Construction of an Advanced ABCD Fragment.

  2001cited by this paper
• The Spongistatins: Architecturally Complex Natural Products-Part Two: Synthesis of the C(29-51) Subunit, Fragment Assembly, and Final Elaboration to (+)-Spongistatin 2.

  2001cited by this paper
• Recent developments in the chemistry, biology and medicine of the epothilones.

  2001cited by this paper
• Total synthesis of (-)-ratjadone.

  2001cited by this paper
• Macrocyclization via allyl transfer: total synthesis of laulimalide.

  2001cited by this paper
• Total synthesis of microtubule-stabilizing agent (-)-laulimalide.

  2001cited by this paper
• The novel cytotoxic sponge metabolite peloruside A, structurally similar to bryostatin-1, has unique bioactivity independent of protein kinase C.

  2001cited by this paper
• The epothilones, eleutherobins, and related types of molecules.

  2001cited by this paper
• Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangement.

  2001cited by this paper
• Synthesis of the macrocyclic core of laulimalide.

  2001cited by this paper
• Total synthesis of (+)-zampanolide.

  2001cited by this paper
• Total synthesis of (+)-ambruticin.

  2001cited by this paper
• Total synthesis of nafuredin, a selective NADH-fumarate reductase inhibitor.

  2001cited by this paper
• Novel molecules that interact with microtubules and have functional activity similar to Taxol.

  2001cited by this paper
• A macrolactonization-based strategy to obtain microtuble-stabilizing agent (-)-laulimalide.

  2001cited by this paper
• An Intramolecular Case of Sharpless Kinetic Resolution: Total Synthesis of Laulimalide.

  2001cited by this paper
• A new antimitotic substance, FR182877. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities.

  2000cited by this paper
• Structure-activity relationship of polyisoprenyl benzophenones from Garcinia pyrifera on the tubulin/microtubule system.

  2000cited by this paper
• Ceric ammonium nitrate on silica gel for efficient and selective removal of trityl and silyl groups

  2000cited by this paper
• Synthesis of B-ring homologated estradiol analogues that modulate tubulin polymerization and microtubule stability.

  2000cited by this paper
• An enantioselective synthesis of the C2-C16 segment of antitumor macrolide laulimalide1.

  2000cited by this paper
• Catalytic Asymmetric Propionate Aldol Reactions via Acyl Halide-Aldehyde Cyclocondensations.

  2000cited by this paper
• Total Synthesis of (-)-Laulimalide.

  2000cited by this paper
• Total syntheses of epothilones B and D.

  2000cited by this paper
• Concise synthesis of (S,S)-(+)-dehydrohomoancepsenolide.

  2000cited by this paper
• Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E.

  2000cited by this paper
• Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the Evans asymmetric alkylation.

  2000cited by this paper
• Peloruside A: a potent cytotoxic macrolide isolated from the new zealand marine sponge Mycale sp.

  2000cited by this paper
• A new antimitotic substance, FR182877. III. Structure determination.

  2000cited by this paper
• Synthetic studies of antitumor macrolide laulimalide: a stereoselective synthesis of the C17-C28 segment.

  2000cited by this paper
• A stereoselective synthesis of (+)-boronolide.

  2000cited by this paper
• Syntheses and biological evaluation of novel pseudomycin side-chain analogues. Part 2.

  2000cited by this paper
• A new antimitotic substance, FR182877. II. The mechanism of action.

  2000cited by this paper
• Total synthesis of (-)-laulimalide.

  2000cited by this paper
• A stereoselective synthesis of (-)-tetrahydrolipstatin.

  1999cited by this paper
• Stabilization of microtubules by Combretastatin D derivatives.

  1999cited by this paper
• Convenient Preparations of (Diphenylphosphono)acetic Acid Esters and the Comparison of the Z-Selectivities of Their Horner-Wadsworth-Emmons Reaction with Aldehydes Depending on the Ester Moiety.

  1999cited by this paper
• Laulimalide and isolaulimalide, new paclitaxel-like microtubule-stabilizing agents.

  1999cited by this paper
• Practical Access to Highly Enantioenriched C-3 Building Blocks via Hydrolytic Kinetic Resolution.

  1998cited by this paper
• Total synthesis of (+)-phorboxazole A.

  1998cited by this paper
• Chemical Biology of Epothilones.

  1998cited by this paper
• RING-CLOSING METATHESIS STRATEGY TO UNSATURATED γ- AND δ-LACTONES: SYNTHESIS OF HYDROXYETHYLENE ISOSTERE FOR PROTEASE INHIBITORS.

  1998cited by this paper
• Effects of tryprostatin derivatives on microtubule assembly in vitro and in situ.

  1998cited by this paper
• SYNTHETIC STUDIES OF ANTITUMOR MACROLIDE LAULIMALIDE: ENANTIOSELECTIVE SYNTHESIS OF THE C3-C14 SEGMENT BY A CATALYTIC HETERO DIELS-ALDER STRATEGY.

  1997cited by this paper
• Total Synthesis of Scytophycin C.

  1997cited by this paper
• GS-164, a small synthetic compound, stimulates tubulin polymerization by a similar mechanism to that of Taxol

  1997cited by this paper
• Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis.

  1997cited by this paper
• Conformationally Constrained Bis(oxazoline) Derived Chiral Catalyst : A Highly Effective Enantioselective Diels-Alder Reaction.

  1996cited by this paper
• Chiral Allylic and Allenic Stannanes as Reagents for Asymmetric Synthesis.

  1996cited by this paper
• ASYMMETRIC HETERO DIELS-ALDER REACTIONS OF DANISHEFSKY'S DIENE AND GLYOXYLATE ESTERS CATALYZED BY CHIRAL BISOXAZOLINE DERIVED CATALYSTS.

  1996cited by this paper
• Stereocontrolled Assembly of Cis or Trans Angularly Substituted Hydrindenes by the Unactivated Intramolecular Diels-Alder Reaction.

  1996cited by this paper

• Discovery of Novel 4,5-Dihydropyrrolo[3,4-c]pyrazol-6(2H)-one-Based Tubulin Inhibitors Targeting Colchicine Binding Site with Potent Anti-Ovarian Cancer Activity.

  2025cites this paper
• Investigating the Structure-Activity Relationship of Laulimalides Marine Macrolides as Promising Inhibitors for SARS-CoV-2 Main Protease (Mpro)

  2024cites this paper
• Stereodivergent assembly of δ-valerolactones with an azaarene-containing quaternary stereocenter enabled by Cu/Ru relay catalysis

  2024cites this paper
• Asymmetric Olefin Isomerization via Photoredox Catalytic Hydrogen Atom Transfer and Enantioselective Protonation.

  2023cites this paper
• Stereoselective Synthesis of Highly Substituted O-Heterocycles via Matteson Homologation: A Ring-Closing Metathesis Approach.

  2023cites this paper
• Re-evaluation of the Fijianolide/Laulimalide Chemotype Suggests an Alternate Mechanism of Action for C-15/C-20 Analogs

  2022cites this paper
• Total Synthesis in the Trost Laboratories: Selected Milestones From the Past Twenty Years

  2021cites this paper
• Formal [5+1] annulation reactions of dielectrophilic peroxides: facile access to functionalized dihydropyrans.

  2020cites this paper
• Functionalized 2-Substituted Allyl Bromides in the Barbier Allylation of (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis of the C8–C17, C8–C18, and C5–C17 Building Blocks of Laulimalides and Their Synthetic Analogs

  2019cites this paper
• Allylation of (R)-2,3-O-Cyclohexylideneglyceraldehyde with Methyl 3-(Bromomethyl)but-3-enoate. Methyl 3-{(2S)-2-[(2R)-1,4-Dioxaspiro[4.5]dec-2-yl]-2-hydroxyethyl}but-3-enoate as a Convenient Universal Building Block for the Synthesis of Key Fragments of Bioactive Compounds

  2019cites this paper
• The journey of total synthesis toward nannocystin Ax

  2019cites this paper
• A General Diastereoselective Strategy for Both cis- and trans-2,6-Disubstituted Tetrahydropyrans: Formal Total Synthesis of (+)-Muconin.

  2018cites this paper
• Synthesis of (2S)-4-Methyl- and (2S)-4-Methyl-6-oxo-3,6-dihydro-2H-pyran-2-carbaldehydes as Precursors to C22–C27 Fragments of Fijianolides and Their Synthetic Analogs

  2018cites this paper
• Early investigational tubulin inhibitors as novel cancer therapeutics

  2016cites this paper
• Applications of oxazolidinones as chiral auxiliaries in the asymmetric alkylation reaction applied to total synthesis

  2016cites this paper
• Cyclopropanol intermediates in the synthesis of the C5–C14 fragment of laulimalides

  2016cites this paper
• Applications of sodium borohydride procedure for the reductive removal of Evans and other chiral auxiliaries

  2016cites this paper
• Chapter 11 – Microtubule Stabilization

  2016cites this paper
• Analysis of the binding mode of laulimalide to microtubules: Establishing a laulimalide–tubulin pharmacophore

  2016cites this paper
• Highly stereocontrolled synthesis of trans-2,6-disubstituted-5-methyl-3,6-dihydropyrans: stereoselective synthesis of the bicyclic core of penostatin B.

  2015cites this paper
• Ester coupling reactions--an enduring challenge in the chemical synthesis of bioactive natural products.

  2015cites this paper
• Tubulin inhibitors: a patent review

  2014cites this paper
• Stereoselective synthesis of the C3–C12 subunit of laulimalide

  2014cites this paper
• Porifera (Sponges)–4

  2014cites this paper
• Porifera (Sponges)–5

  2014cites this paper
• Hydrogen-bond-directed formal [5 + 1] annulations of oxindoles with ester-linked bisenones: facile access to chiral spirooxindole δ-lactones.

  2014cites this paper
• Cytoskeleton and Human Disease

  2012cites this paper
• Enantioselective synthesis of 2,6-cis-disubstituted tetrahydropyrans via a tandem catalytic asymmetric hydrogenation/oxa-Michael cyclization: an efficient approach to (-)-centrolobine.

  2012cites this paper
• Microtubules as a Target in Cancer Therapy

  2012cites this paper
• Stereoselective synthesis of 2,6-trans-tetrahydropyrans.

  2012cites this paper
• Total synthesis of laulimalide: synthesis of the northern and southern fragments.

  2012cites this paper
• Marine natural products.

  2012cites this paper
• Microtubule stabilizing agents as potential treatment for Alzheimer's disease and related neurodegenerative tauopathies.

  2012cites this paper
• Stereoselective synthesis of five biologically active, naturally occurring medium and large ring lactones.

  2011cites this paper
• Stereoselective Synthesis of Five Biologically Active, Naturally Occurring Medium and Large Ring Lactones

  2011cites this paper
• Role of the Cytoskeleton in Formation and Maintenance of Angiogenic Sprouts

  2011cites this paper
• Lewis-acid catalyzed formation of dihydropyrans

  2011cites this paper
• Catalytic asymmetric formation of delta-lactones from unsaturated acyl halides.

  2010cites this paper
• The laulimalide family: total synthesis and biological evaluation of neolaulimalide, isolaulimalide, laulimalide and a nonnatural analogue.

  2009cites this paper
• Synthesis, Biological Evaluation of 1,1‐Diarylethylenes as a Novel Class of Antimitotic Agents

  2009cites this paper
• Biomimetic transannular oxa-conjugate addition approach to the 2,6-disubstituted dihydropyran of laulimalide yields an unprecedented transannular oxetane.

  2009cites this paper
• Macrolide-based microtubule-stabilizing agents - chemistry and structure-activity relationships.

  2009cites this paper
• Synthesis and biological evaluation of a des-dihydropyran laulimalide analog

  2009cites this paper
• Microtubule stabilising agents for cancer chemotherapy

  2009cites this paper
• Asymmetric synthesis of Goniothalesdiol A from (R)-2,3-O-cyclohexylidine glyceraldehyde

  2009cites this paper
• Marine macrolides, a promising source of antitumor compounds.

  2009cites this paper
• A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

  2009cites this paper
• Function-oriented synthesis, step economy, and drug design.

  2008cites this paper
• Total synthesis of neolaulimalide and isolaulimalide.

  2008cites this paper
• Alcohol-assisted phosphine catalysis: one-step syntheses of dihydropyrones from aldehydes and allenoates.

  2008cites this paper
• Catalytic Asymmetric Formation of δ‐Lactones by [4+2] Cycloaddition of Zwitterionic Dienolates Generated from α,β‐Unsaturated Acid Chlorides

  2007cites this paper
• Sponge-derived fijianolide polyketide class: further evaluation of their structural and cytotoxicity properties.

  2007cites this paper
• Microtubule-stabilizing natural products as promising cancer therapeutics.

  2007cites this paper
• 1.08 – Natural Product Sources of Drugs: Plants, Microbes, Marine Organisms, and Animals

  2007cites this paper
• Ring-closing Olefin Metathesis for Organic Synthesis

  2007cites this paper
• Anticancer drugs from nature--natural products as a unique source of new microtubule-stabilizing agents.

  2007cites this paper
• Catalytic asymmetric formation of delta-lactones by [4+2] cycloaddition of zwitterionic dienolates generated from alpha,beta-unsaturated acid chlorides.

  2007cites this paper
• Katalytische asymmetrische Synthese von δ‐Lactonen durch [4+2]‐Cycloaddition von zwitterionischen Dienolaten, erzeugt aus α,β‐ungesättigten Säurechloriden

  2007cites this paper
• Synthetic studies on a phenyl-laulimalide analogue

  2006cites this paper
• Highly Efficient Approach to 4‐Ethoxy‐5,6‐dihydro‐6,6‐disubstituted Pyran‐2‐ones using a Combinational Lewis Acid‐Base System

  2006cites this paper
• Apoptolidin: induction of apoptosis by a natural product.

  2006cites this paper
• Natural products from marine invertebrates and microbes as modulators of antitumor targets.

  2006cites this paper
• Highly enantio- and diastereoselective Brassard type hetero-Diels-Alder approach to 5-methyl-containing alpha,beta-unsaturated delta-lactones.

  2006cites this paper
• Apoptolidin: Induktion von Apoptose durch einen Naturstoff

  2006cites this paper
• The Literature of Heterocyclic Chemistry, Part IX, 2002–2004

  2006cites this paper
• Marine natural products.

  2005cites this paper
• Marine natural products: synthetic aspects.

  2005cites this paper
• Total synthesis of (-)-laulimalide: Pd-catalyzed stereospecific ring construction of the substituted 3,6-dihydro[2H]pyran units.

  2005cites this paper
• Marine natural products: synthetic aspects.

  2005cites this paper
• Stereoselective synthesis of c3-c12 dihydropyran portion of antitumor laulimalide using copper-catalyzed oxonium ylide formation-[2,3] shift.

  2005cites this paper
• Synthesis of 9- and 10-membered macrolactones by selective ozonolysis of 1,4-diazaphenanthrene derivatives

  2005cites this paper
• Conformational studies and solution structure of laulimalide and simplified analogues using NMR spectroscopy and molecular modelling

  2005cites this paper
• The Discovery of Anticancer Drugs From Natural Sources

  2005cites this paper
• Design, synthesis and biological evaluation of novel, simplified analogues of laulimalide: modification of the side chain.

  2005cites this paper
• Synthesis of 8-(S)-methoxy-11-desmethyl laulimalide: a novel laulimalide analogue

  2005cites this paper
• A Mild and Efficient Asymmetric Hetero‐Diels–Alder Reaction of the Brassard Diene with Aldehydes

  2005cites this paper
• Stereoselective preparation of trisubstituted (Z)-alkenes; synthesis of the C17–C27 fragment of (−)-laulimalide

  2005cites this paper
• Advances in the total synthesis of biologically important marine macrolides.

  2005cites this paper
• Natural product-like chemical space: search for chemical dissectors of macromolecular interactions.

  2005cites this paper
• Total synthesis of the boron-containing ion carrier antibiotic macrodiolide tartrolon B.

  2004cites this paper
• Highly enantioselective hetero-Diels-Alder reaction of Brassard diene with aromatic aldehydes.

  2004cites this paper
• Synthesis of novel 11-desmethyl analogues of laulimalide by Nozaki-Kishi coupling.

  2004cites this paper
• Marine natural products and related compounds in clinical and advanced preclinical trials.

  2004cites this paper
• Advanced preclinical and clinical trials of natural products and related compounds from marine sources.

  2004cites this paper
• Computational comparison of microtubule-stabilising agents laulimalide and peloruside with taxol and colchicine.

  2004cites this paper
• Microtubule-Stabilizing Marine Metabolite Laulimalide and Its Derivatives: Synthetic Approaches and Antitumor Activity

  2003cites this paper
• Development of Laulimalide-Based Microtubule-Stabilizing Agents: New Chemistry for the Treatment of Breast Cancer

  2002cites this paper