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Total Synthesis of (+)‐Halichlorine: An Inhibitor of VCAM‐1 Expression

Total Synthesis of (+)‐Halichlorine: An Inhibitor of VCAM‐1 Expression 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=tert‐butyldimethylsilyl. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Angewandte Chemie International Edition Wiley

Total Synthesis of (+)‐Halichlorine: An Inhibitor of VCAM‐1 Expression

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Publisher
Wiley
Copyright
Copyright © 1999 WILEY‐VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany
ISSN
1433-7851
eISSN
1521-3773
DOI
10.1002/(SICI)1521-3773(19991203)38:23<3542::AID-ANIE3542>3.0.CO;2-I
Publisher site
See Article on Publisher Site

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=tert‐butyldimethylsilyl.

Journal

Angewandte Chemie International Edition – Wiley

Published: Dec 3, 1999

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