Literature DB >> 10602236

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

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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.

Entities:  

Year:  1999        PMID： 10602236     DOI： 10.1002/(sici)1521-3773(19991203)38:23<3542::aid-anie3542>3.0.co;2-i

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Iminium Ion Cascade Reactions: Stereoselective Synthesis of Quinolizidines and Indolizidines.

Authors:  Shawn M Amorde; Ivan T Jewett; Stephen F Martin
Journal:  Tetrahedron       Date:  2009-04-19       Impact factor: 2.457

2.  Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine.

Authors:  Rodrigo B Andrade; Stephen F Martin
Journal:  Org Lett       Date:  2005-12-08       Impact factor: 6.005

3.  Total synthesis of quinolizidine alkaloid (-)-217A. Application of iminoacetonitrile cycloadditions in organic synthesis.

Authors:  Kevin M Maloney; Rick L Danheiser
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

4.  Enantioselective synthesis of angularly substituted 1-azabicylic rings: coupled dynamic kinetic epimerization and chirality transfer.

Authors:  Zachary D Aron; Tatsuya Ito; Tricia L May; Larry E Overman; Jocelyn Wang
Journal:  J Org Chem       Date:  2013-09-10       Impact factor: 4.354

5.  Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: synthetic studies toward halichlorine.

Authors:  Gary E Keck; Stacey A Heumann
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

6.  Recent Applications of Imines as Key Intermediates in the Synthesis of Alkaloids and Novel Nitrogen Heterocycles.

Authors:  Stephen F Martin
Journal:  Pure Appl Chem       Date:  2009       Impact factor: 2.453

7.  Total synthesis of (+/-)-halichlorine, (+/-)-pinnaic acid, and (+/-)-tauropinnaic acid.

Authors:  Hamish S Christie; Clayton H Heathcock
Journal:  Proc Natl Acad Sci U S A       Date:  2004-08-06       Impact factor: 11.205
  7 in total

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