A concise and stereoselective synthesis of squalamine

Dong Hui Zhang; Feng Cai; Xiang Dong Zhou; Wei Shan Zhou

doi:10.1021/ol035062j

A concise and stereoselective synthesis of squalamine

Dong Hui Zhang, Feng Cai, Xiang Dong Zhou, Wei Shan Zhou

Research output: Contribution to journal › Article › peer-review

35 Scopus citations

Abstract

(Matrix presented) 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.

Original language	English (US)
Pages (from-to)	3257-3259
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	18
DOIs	https://doi.org/10.1021/ol035062j
State	Published - Sep 4 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol035062j

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title = "A concise and stereoselective synthesis of squalamine",

abstract = "(Matrix presented) 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.",

author = "Zhang, {Dong Hui} and Feng Cai and Zhou, {Xiang Dong} and Zhou, {Wei Shan}",

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AU - Cai, Feng

AU - Zhou, Xiang Dong

AU - Zhou, Wei Shan

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N2 - (Matrix presented) 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.

AB - (Matrix presented) 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.

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A concise and stereoselective synthesis of squalamine

Abstract

ASJC Scopus subject areas

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