Stereoselective synthesis of squalamine dessulfate

Robert M. Moriarty; Livia A. Enache; William A. Kinney; Craig S. Allen; James W. Canary; Sudersan M. Tuladhar; Liang Guo

Stereoselective synthesis of squalamine dessulfate

Robert M. Moriarty, Livia A. Enache, William A. Kinney, Craig S. Allen, James W. Canary, Sudersan M. Tuladhar, Liang Guo

Chemistry

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

Abstract

Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol. The key step in establishing the C24 stereochemistry is attachment of the side-chain at C22 using either (2R)- or (2S)-1,2-epoxy-3-methylbutane to yield the cholesteryl precursors of the epimeric squalamine dessulfates.

Original language	English (US)
Pages (from-to)	5139-5142
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	29
State	Published - 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Cite this

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title = "Stereoselective synthesis of squalamine dessulfate",

abstract = "Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol. The key step in establishing the C24 stereochemistry is attachment of the side-chain at C22 using either (2R)- or (2S)-1,2-epoxy-3-methylbutane to yield the cholesteryl precursors of the epimeric squalamine dessulfates.",

author = "Moriarty, {Robert M.} and Enache, {Livia A.} and Kinney, {William A.} and Allen, {Craig S.} and Canary, {James W.} and Tuladhar, {Sudersan M.} and Liang Guo",

year = "1995",

language = "English (US)",

volume = "36",

pages = "5139--5142",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "29",

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TY - JOUR

T1 - Stereoselective synthesis of squalamine dessulfate

AU - Moriarty, Robert M.

AU - Enache, Livia A.

AU - Kinney, William A.

AU - Allen, Craig S.

AU - Canary, James W.

AU - Tuladhar, Sudersan M.

AU - Guo, Liang

PY - 1995

Y1 - 1995

N2 - Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol. The key step in establishing the C24 stereochemistry is attachment of the side-chain at C22 using either (2R)- or (2S)-1,2-epoxy-3-methylbutane to yield the cholesteryl precursors of the epimeric squalamine dessulfates.

AB - Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol. The key step in establishing the C24 stereochemistry is attachment of the side-chain at C22 using either (2R)- or (2S)-1,2-epoxy-3-methylbutane to yield the cholesteryl precursors of the epimeric squalamine dessulfates.

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UR - http://www.scopus.com/inward/citedby.url?scp=0029046881&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0029046881

SN - 0040-4039

VL - 36

SP - 5139

EP - 5142

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -

Stereoselective synthesis of squalamine dessulfate

Abstract

ASJC Scopus subject areas

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