A concise and stereoselective synthesis of squalamine.

[reaction: see text] A short and highly stereoselective synthesis of the novel steroid squalamine (1) was accomplished in nine steps from easily available methyl chenodeoxylcholanate 2. Our synthesis featured improved dehydrogenation of 4 followed by conjugate reduction to construct the trans AB-ring system and efficient asymmetric isopropylation of aldehyde 6 to introduce the C-24R-hydroxyl group.

• Publication year

  2003

• Venue

  Organic Letters

• Publication date

  2003-08-15

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1002/CHIN.200352195PMID 12943401
• 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.

• A stereoselective synthesis of squalamine

  2002cited by this paper
• Modulation of the reactivity profile of IBX by ligand complexation: ambient temperature dehydrogenation of aldehydes and ketones to alpha,beta-unsaturated carbonyl compounds.

  2002cited by this paper
• Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes.

  2002cited by this paper
• Modulation of the Reactivity Profile of IBX by Ligand Complexation: Ambient Temperature Dehydrogenation of Aldehydes and Ketones to α,β‐Unsaturated Carbonyl Compounds

  2002cited by this paper
• Squalamine and cisplatin block angiogenesis and growth of human ovarian cancer cells with or without HER-2 gene overexpression

  2002cited by this paper
• A phase I and pharmacokinetic study of squalamine, a novel antiangiogenic agent, in patients with advanced cancers.

  2001cited by this paper
• Squalamine treatment of human tumors in nu/nu mice enhances platinum-based chemotherapies.

  2001cited by this paper
• A short formal synthesis of squalamine from a microbial metabolite.

  2000cited by this paper
• A New Method for the One-Step Synthesis of α,β-Unsaturated Carbonyl Systems from Saturated Alcohols and Carbonyl Compounds

  2000cited by this paper
• Synthesis of Squalamine Utilizing a Readily Accessible Spermidine Equivalent

  1998cited by this paper
• Squalamine inhibits angiogenesis and solid tumor growth in vivo and perturbs embryonic vasculature.

  1998cited by this paper
• Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol

  1995cited by this paper
• Synthesis of 24.xi.-Squalamine, an Anti-Infective Steroidal Polyamine

  1995cited by this paper
• Stereoselective synthesis of squalamine dessulfate

  1995cited by this paper
• Synthesis of squalamine. A steroidal antibiotic from the shark

  1994cited by this paper
• Déjà vu guides the way to new antimicrobial steroid.

  1993cited by this paper
• Squalamine: an aminosterol antibiotic from the shark.

  1993cited by this paper
• Synthesis of the 1 beta-hydroxylated bile acids and identification of 1 beta,3 alpha,7 alpha-trihydroxy- and 1 beta,3 alpha,7 alpha,12 alpha-tetrahydroxy-5 beta-cholan-24-oic acids in human meconium.

  1985cited by this paper
• Synthesis of the 1β-hydroxylated bile acids and identification of 1β,3α,7α-trihydroxy- and 1β,3α,7α,12α-tetrahydroxy-5β-cholan-24-oic acids in human meconium

  1985cited by this paper

• Construction of the chiral 24R-OH squalamine intermediate by an engineered ketoreductase from Rhodococcus sp.

  2026cites this paper
• Bile acid resource compounds: reactions and applications in natural products synthesis

  2025cites this paper
• Squalamines in Blockade of Tumor-Associated Angiogenesis and Cancer Progression

  2022cites this paper
• From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

  2022cites this paper
• Synthesis and Biological Activities of Natural Functionalized Polyamines: An Overview.

  2020cites this paper
• Study on Synthesis of Key Squalamine intermediate 7α, 24R -Dihydroxy-5α-cholestan-3-one.

  2019cites this paper
• A squalamine derivative, NV669, as a novel PTP1B inhibitor: in vitro and in vivo effects on pancreatic and hepatic tumor growth

  2019cites this paper
• Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations

  2017cites this paper
• Anti-­Infective Agents from Marine Sources

  2015cites this paper
• A concise account of various approaches for stereoselective construction of the C-20(H) stereogenic center in steroid side chain.

  2014cites this paper
• Vertebrates: Fish, Reptiles, and Mammals

  2014cites this paper
• 7.06 Oxidation Adjacent to CX Bonds by Dehydrogenation

  2014cites this paper
• N-cholesteryl amino acid conjugates and their antimicrobial activities.

  2013cites this paper
• A concise synthesis and antimicrobial activities of 3-polyamino-23,24-bisnorcholanes as steroid-polyamine conjugates.

  2011cites this paper
• Squalamine ointment for Staphylococcus aureus skin decolonization in a mouse model.

  2011cites this paper
• 2-Iodoxybenzoic acid--a simple oxidant with a dazzling array of potential applications.

  2011cites this paper
• 2‐Iodoxybenzoesäure – ein einfaches Oxidationsmittel mit einer Vielfalt an Anwendungsmöglichkeiten

  2011cites this paper
• Aza-annulation on the 16-dehydropregnenolone, via tandem intermolecular aldol process and intramolecular Michael addition.

  2011cites this paper
• Synthesis of an analogue of squalamine: 6β‐hydroxyl‐3‐aminosterol

  2010cites this paper
• Synthesis of 3-Benzoyl Acrylates/Acrylamides via Dehydrogenation of 3-Benzoyl Propionates/Propionamides Using IBX/p-TsOH

  2010cites this paper
• Second-generation synthesis of endogenous sperm-activating and attracting factor (SAAF) isolated from the ascidian Ciona intestinalis

  2010cites this paper
• Syntheses of two new components of sea lamprey migratory pheromone and synthetic efforts towards hirsutellones A, B, C, and F.

  2010cites this paper
• Synthesis and biological activities of 3-polyamino-5β-cholane-7α,24-diols

  2009cites this paper
• Design and synthesis of bile acid-based amino sterols as antimicrobial agents.

  2009cites this paper
• Synthesis and antimicrobial activity of 7 alpha-amino-23,24-bisnor-5 alpha-cholan-22-ol derivatives.

  2008cites this paper
• Parâmetros de carga para o campo de força e análise estrutural do aminoesteróide esqualamina

  2008influential citation
• Parâmetros de Carga para o Campo de Força e Análise Estrutural do Aminoesteróide Esqualamina

  2008cites this paper
• A critical review of the discovery and application of a migratory pheromone in an invasive fish, the sea lamprey Petromyzon marinus L.

  2007cites this paper
• Stereoselective syntheses of 20-epi cholanic acid derivatives from 16-dehydropregnenolone acetate

  2007cites this paper
• Details of the structure determination of the sulfated steroids PSDS and PADS: new components of the sea lamprey (petromyzon marinus) migratory pheromone.

  2007cites this paper
• Synthesis of Gymnasterone B, an antitumor steroid from Gymnascella dankaliensis

  2006cites this paper
• Steroidal conjugates and their pharmacological applications.

  2006cites this paper
• Utilizing the Power of Microbial Genetics to Bridge the Gap Between the Promise and the Application of Marine Natural Products

  2005cites this paper
• Polyamine alkaloids.

  2005cites this paper
• A Short and Highly Stereoselective Synthesis of Squalamine from Methyl Chenodeoxycholanate

  2005cites this paper
• Mixture of new sulfated steroids functions as a migratory pheromone in the sea lamprey

  2005cites this paper