A Short and Highly Stereoselective Synthesis of Squalamine from Methyl Chenodeoxycholanate | Zendy

DongHui Zhang | Zendy; Feng Cai | Zendy; XiangDong Zhou | Zendy; WeiShan Zhou | Zendy

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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.

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