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A Short and Highly Stereoselective Synthesis of Squalamine from Methyl Chenodeoxycholanate
Author(s) -
DongHui Zhang,
Feng Cai,
XiangDong Zhou,
WeiShan Zhou
Publication year - 2005
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200590176
Subject(s) - chemistry , stereoselectivity , dehydrogenation , conjugate , aldehyde , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , mathematical analysis , mathematics
A short and highly stereoselective synthesis of squalamine ( 1 ) was accomplished in 9 steps from easily available methyl chenodeoxycholanate ( 2 ). The advanced intermediate 7α,24 R ‐dihydroxy‐cholestan‐3‐one ( 9 ) was synthesized by using improved dehydrogenation of 4 followed by conjugate reduction and efficient asymmetric isopropylation of aldehyde 7 as key reactions.