Communication
Total Synthesis of (+)-Halichlorine: An Inhibitor of VCAM-1 Expression
First published: 30 November 1999
Citations: 115
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.
