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

doi:10.1016/00404-0399(50)10116-

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 sidechain 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
DOIs	https://doi.org/10.1016/00404-0399(50)10116-
State	Published - Jul 17 1995

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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 sidechain 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",

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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 - 1995/7/17

Y1 - 1995/7/17

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 sidechain 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 sidechain 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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EP - 5142

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 29

ER -