Highly Stereoselective Total Synthesis of (+)‐9‐epi‐Dictyostatin and (–)‐12,13‐Bis‐epi‐dictyostatin

No abstract is available for this paper.

• Publication year

  2011

• Venue

  European Journal of Organic Chemistry

• Publication date

  2011-05-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1002/EJOC.201100244
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Dictyostatin flexibility bridges conformations in solution and in the β-tubulin taxane binding site.

  2011cited by this paper
• Stereoselective synthesis of the C15-C26 fragment of the antitumor agent (-)-dictyostatin.

  2011cited by this paper
• Total synthesis and biological evaluation of a series of macrocyclic hybrids and analogues of the antimitotic natural products dictyostatin, discodermolide, and taxol.

  2011cited by this paper
• Total synthesis of (-)-dictyostatin, a microtubule-stabilising anticancer macrolide of marine sponge origin

  2010cited by this paper
• Total synthesis of a library of designed hybrids of the microtubule-stabilising anticancer agents taxol, discodermolide and dictyostatin.

  2010cited by this paper
• Streamlined syntheses of (-)-dictyostatin, 16-desmethyl-25,26-dihydrodictyostatin, and 6-epi-16-desmethyl-25,26-dihydrodictyostatin.

  2010cited by this paper
• Overriding Felkin control: a general method for highly diastereoselective chelation-controlled additions to alpha-silyloxy aldehydes.

  2010cited by this paper
• A Highly Stereoselective Total Synthesis of (+)-9-epi-Dictyostatin

  2010cited by this paper
• Studies Directed Towards the Total Synthesis of (–)‐Dictyostatin

  2010cited by this paper
• A formal total synthesis of dictyostatin

  2009cited by this paper
• Synthesis of the C11–C23 Fragment of the Potent Antitumor Agent Dictyostatin

  2009cited by this paper
• Total synthesis and biological evaluation of novel C2-C6 region analogues of dictyostatin.

  2009cited by this paper
• Michael addition-elimination reactions of chiral enolates with ethyl 3-halopropenoates.

  2008cited by this paper
• Total synthesis of a potent hybrid of the anticancer natural products dictyostatin and discodermolide.

  2008cited by this paper
• Synthesis and biological evaluation of ( − )-dictyostatin and stereoisomers

  2008cited by this paper
• Improved synthesis of 6-epi-dictyostatin and antitumor efficacy in mice bearing MDA-MB231 human breast cancer xenografts.

  2008cited by this paper
• The bound conformation of microtubule-stabilizing agents: NMR insights into the bioactive 3D structure of discodermolide and dictyostatin.

  2008cited by this paper
• Total synthesis and biological evaluation of potent analogues of dictyostatin: modification of the C2-C6 dienoate region.

  2008cited by this paper
• Total synthesis of potential antitumor agent, (-)-dictyostatin.

  2007cited by this paper
• Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.

  2007cited by this paper
• Total synthesis and biological evaluation of C16 analogs of (-)-dictyostatin.

  2007cited by this paper
• Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites.

  2007cited by this paper
• Synthesis and biological evaluation of novel analogues of dictyostatin.

  2007cited by this paper
• Design, synthesis and biological evaluation of a macrocyclic discodermolide/dictyostatin hybrid.

  2007cited by this paper
• A two-directional approach to a (-)-dictyostatin C11-C23 segment: development of a highly diastereoselective, kinetically-controlled Meerwein-Ponndorf-Verley reduction.

  2007cited by this paper
• Overcoming Tumor Drug Resistance with High‐Affinity Taxanes: A SAR Study of C2‐Modified 7‐Acyl‐10‐Deacetyl Cephalomannines

  2007cited by this paper
• Synthesis of the C15–C23 fragment of dictyostatin using a highly stereoselective Carreira alkynylation

  2007cited by this paper
• A highly stereoselective synthesis of the C10-C23 fragment of (-)-dictyostatin.

  2007cited by this paper
• Chemoenzymatic synthesis of the C10-C23 segment of dictyostatin.

  2006cited by this paper
• Total synthesis of (-)-dictyostatin.

  2006cited by this paper
• Fluorous mixture synthesis of (-)-dictyostatin and three stereoisomers.

  2006cited by this paper
• A cross metathesis approach to the synthesis of the C11–C23 fragment of (−)-16-normethyldictyostatin☆

  2006cited by this paper
• Synthesis and biological evaluation of (-)-16-normethyldictyostatin: a potent analogue of (-)-dictyostatin.

  2005cited by this paper
• Tubulin assembly, taxoid site binding, and cellular effects of the microtubule-stabilizing agent dictyostatin.

  2005cited by this paper
• Ring-closing metathesis approach to dictyostatin.

  2005cited by this paper
• Microtubule interactions with chemically diverse stabilizing agents: thermodynamics of binding to the paclitaxel site predicts cytotoxicity.

  2005cited by this paper
• Total synthesis and configurational assignment of (-)-dictyostatin, a microtubule-stabilizing macrolide of marine sponge origin.

  2004cited by this paper
• Stereochemical determination of dictyostatin, a novel microtubule-stabilising macrolide from the marine sponge Corallistidae sp.

  2004cited by this paper
• Total synthesis of (-)-dictyostatin: confirmation of relative and absolute configurations.

  2004cited by this paper
• Alkene-alkyne coupling as a linchpin: an efficient and convergent synthesis of amphidinolide P.

  2004cited by this paper
• Titanium(II)-mediated Cyclization of (Silyloxy)enynes: A Synthesis of the C9–C19 Subunit of Dictyostatin-1

  2004cited by this paper
• Interaction of epothilone analogs with the paclitaxel binding site: relationship between binding affinity, microtubule stabilization, and cytotoxicity.

  2004cited by this paper
• Tubulin polymerizing activity of dictyostatin-1, a polyketide of marine sponge origin.

  2003cited by this paper
• Discodermolide/Dictyostatin hybrids: synthesis and biological evaluation.

  2002cited by this paper
• Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions.

  2002cited by this paper
• Total Synthesis of Fostriecin (CI‐920)

  2001cited by this paper
• Total Synthesis of Apoptolidin: Part 1. Retrosynthetic Analysis and Construction of Building Blocks.

  2001cited by this paper
• The exceptional chelating ability of dimethylaluminum chloride and methylaluminum dichloride. The merged stereochemical impact of alpha- and beta-stereocenters in chelate-controlled carbonyl addition reactions with enolsilane and hydride nucleophiles.

  2001cited by this paper
• Synthesis and Reactions of Allylic, Allenic, Vinylic, and Arylmetal Reagents from Halides and Esters via Transient Organopalladium Intermediates.

  2000cited by this paper
• Evolution of a Gram-Scale Synthesis of (+)-Discodermolide

  2000cited by this paper
• Facile Enantioselective Synthesis of Propargylic Alcohols by Direct Addition of Terminal Alkynes to Aldehydes

  2000cited by this paper
• Total Synthesis of (+)-Amphidinolide J

  1998cited by this paper
• Pseudoephedrine as a Practical Chiral Auxiliary for the Synthesis of Highly Enantiomerically Enriched Carboxylic Acids, Alcohols, Aldehydes, and Ketones

  1997cited by this paper
• Total Synthesis of (−)-Discodermolide: An Application of a Chelation-Controlled Alkylation Reaction

  1997cited by this paper
• A Stereochemical Model for Merged 1,2- and 1,3-Asymmetric Induction in Diastereoselective Mukaiyama Aldol Addition Reactions and Related Processes

  1996cited by this paper
• Propargylation of Carbonyl Compounds by Umpolung of Propargylpalladium Complexes with Diethylzinc

  1996cited by this paper
• An Improved One-pot Procedure for the Synthesis of Alkynes from Aldehydes

  1996cited by this paper
• Studies Towards the Total Synthesis of the Marine-Derived Immunosuppressant Discodermolide: Stereoselective Synthesis of a C9-C24 Subunit

  1995cited by this paper
• Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by Chiral Ruthenium(II) Complexes

  1995cited by this paper
• Extension of the Colvin Rearrangement Using Trimethylsilyldiazomethane. A New Synthesis of Alkynes

  1994cited by this paper
• Tetrapropylammonium Perruthenate, Pr4N+RuO4 -, TPAP: A Catalytic Oxidant for Organic Synthesis

  1994cited by this paper
• Analysis of two carbon-13 NMR correlations for determining the stereochemistry of 1,3-diol acetonides

  1993cited by this paper
• Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds

  1989cited by this paper
• On the selectivity of deprotection of benzyl, mpm (4-methoxybenzyl) and dmpm (3,4-dimethoxybenzyl) protecting groups for hydroxy functions

  1986cited by this paper
• Elaboration of aldehydes and ketones to alkynes: improved methodology

  1979cited by this paper
• A rapid esterification by means of mixed anhydride and its application to large-ring lactonization.

  1979cited by this paper
• Rapid chromatographic technique for preparative separations with moderate resolution

  1978cited by this paper
• One-step conversion of carbonyl compounds into acetylenes

  1973cited by this paper
• A synthetic method for formyl→ethynyl conversion (RCHO→RCCH or RCCR′)

  1972cited by this paper
• Reactions of dimethylphosphono-substituted diazoalkanes. (MeO)2P(O)CR transfer to olefins and 1,3-dipolar additions of (MeO)2P(O)C(N2)R

  1971cited by this paper

• Enantioselective Total Synthesis of (+)-Heilonine

  2021cites this paper
• Structural Determinants of the Dictyostatin Chemotype for Tubulin Binding Affinity and Antitumor Activity Against Taxane- and Epothilone-Resistant Cancer Cells

  2016cites this paper
• Dictyoceratidan poisons: Defined mark on microtubule-tubulin dynamics.

  2016cites this paper
• Conformation-activity relationships of polyketide natural products.

  2015cites this paper
• Structure elucidation of nigricanoside A through enantioselective total synthesis

  2015cites this paper
• Probing o-diphenylphosphanyl benzoate (o-DPPB)-directed C-C bond formation: total synthesis of dictyostatin.

  2015cites this paper
• Approaches to the total synthesis of chaetochalasin A.

  2014cites this paper
• Reduction of CåC and CåC by Noncatalytic Chemical Methods

  2014cites this paper
• Asymmetric total synthesis of (−)-rasfonin

  2013cites this paper
• A highly step-economical synthesis of dictyostatin.

  2013cites this paper
• Update 1 of: macrolactonizations in the total synthesis of natural products.

  2013cites this paper
• Stereoselectivity in (Z)‐Vinylmetal Additions to the Dictyostatin C1–C9 β‐Silyloxy Aldehyde

  2012cites this paper
• Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents

  2011cites this paper