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A Short and Highly Stereoselective Synthesis of Squalamine from Methyl Chenodeoxycholanate

✍ Scribed by Zhang Dong-Hui; Cai Feng; Zhou Xiang-Dong; Zhou Wei-Shan

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 76 KB
Volume: 23
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.200590176

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✦ Synopsis

A short and highly stereoselective synthesis of squalamine (1) was accomplished in 9 steps from easily available methyl chenodeoxycholanate (2). The advanced intermediate 7α,24R-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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