Total synthesis of (+)-halichlorine

An inhibitor of VCAM-1 expression

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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)3542-3545
Number of pages4
JournalAngewandte Chemie - International Edition
Volume38
Issue number23
DOIs
StatePublished - Dec 3 1999

Fingerprint

Vascular Cell Adhesion Molecule-1
Amino alcohols
Amino Alcohols
Cell adhesion
Cell Adhesion Molecules
Aldehydes
Molecules
halichlorine

Keywords

  • Alkaloids
  • C-C coupling
  • Natural products
  • Organozinc compounds
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Total synthesis of (+)-halichlorine : An inhibitor of VCAM-1 expression. / Trauner, Dirk; Schwarz, Jacob B.; Danishefsky, Samuel J.

In: Angewandte Chemie - International Edition, Vol. 38, No. 23, 03.12.1999, p. 3542-3545.

Research output: Contribution to journalArticle

Trauner, Dirk ; Schwarz, Jacob B. ; Danishefsky, Samuel J. / Total synthesis of (+)-halichlorine : An inhibitor of VCAM-1 expression. In: Angewandte Chemie - International Edition. 1999 ; Vol. 38, No. 23. pp. 3542-3545.
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