title: A concise and stereoselective synthesis of squalamine.
abstract: [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.
authors.affiliation: Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
authors.forename: Dong-Hui
authors.initials: DH
authors.lastname: Zhang
authors.forename: Feng
authors.initials: F
authors.lastname: Cai
authors.forename: Xiang-Dong
authors.initials: XD
authors.lastname: Zhou
authors.forename: Wei-Shan
authors.initials: WS
authors.lastname: Zhou
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002757:Cholanes / Q000737:chemistry; D002777:Cholestanols / Q000138:chemical synthesis*; D006900:Hydroxylation; D008024:Ligands; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D002757:Cholanes; D002777:Cholestanols; D008024:Ligands; C079655:squalamine