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.
Zhang
Dong-Hui
DH
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
Cai
Feng
F
Zhou
Xiang-Dong
XD
Zhou
Wei-Shan
WS
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
D000447:Aldehydes; D000970:Antineoplastic Agents; D002757:Cholanes; D002777:Cholestanols; D008024:Ligands; C079655:squalamine