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

  


Authors: Trauner, D.; Schwarz, J. B.; Danishefsky, S. J.
Article Title: Total synthesis of (+)-halichlorine: An inhibitor of VCAM-1 expression
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.
Keywords: vascular cell adhesion molecule 1; chemical structure; alkaloids; chemical reaction; synthesis; total synthesis; stereochemistry; diastereoisomer; natural products; chemical binding; aldehyde; article; c-c coupling; chlorine derivative; organozinc compounds; aminoalcohol
Journal Title: Angewandte Chemie - International Edition
Volume: 38
Issue: 23
ISSN: 1433-7851
Publisher: Wiley Blackwell  
Date Published: 1999-12-03
Start Page: 3542
End Page: 3545
Language: English
DOI: 10.1002/(sici)1521-3773(19991203)38:23<3542::aid-anie3542>3.0.co;2-i
PROVIDER: scopus
DOI/URL:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0033521184&partnerID=40&md5=3b72866372aa99a75fd240180b034624
Notes: Article -- Export Date: 16 August 2016 -- Source: Scopus
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MSK Authors
  1. Jacob B Schwarz
    9 Schwarz
  2. Dirk Trauner
    4 Trauner
  3. Samuel J Danishefsky
    539 Danishefsky
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