Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression

Dirk Trauner; Jacob B. Schwarz; Samuel J. Danishefsky

doi:10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression

Dirk Trauner, Jacob B. Schwarz, Samuel J. Danishefsky

Chemistry

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

Abstract

The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (→4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS = tertbutyldimethylsilyl.

Original language	English (US)
Pages (from-to)	3542-3545
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	38
Issue number	23
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I
State	Published - Dec 3 1999

Keywords

Alkaloids
C-C coupling
Natural products
Organozinc compounds
Total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I

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AU - Danishefsky, Samuel J.

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AB - The diastereoselective addition of the highly functionalized organozinc compound 1 to the aldehyde 2 in the presence of the chiral amino alcohol 3 (→4) is a key step in the first total synthesis of (+)-halichlorine. A series of protections/deprotections and a macrolaconization complete the synthesis. Halichlorine selectively inhibits the expression of the cell adhesion molecule VCAM-1. TBS = tertbutyldimethylsilyl.

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KW - C-C coupling

KW - Natural products

KW - Organozinc compounds

KW - Total synthesis

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Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression

Abstract

Keywords

ASJC Scopus subject areas

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