Convergent Highly Stereoselective Preparation of the C12−C24 Fragment of Macrolactin A

The convergent synthesis of the C12−C24 fragment (lower part) of macrolactin A is described. The adapted strategy allowed building up the lower moiety by the assembly of three key intermediates via organometallic addition. One hydroxylic stereogenic center was introduced by the application of chiral...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-07, Vol.69 (15), p.5015-5022
Main Authors: Bonini, Carlo, Chiummiento, Lucia, Pullez, Maddalena, Solladié, Guy, Colobert, Françoise
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Summary:The convergent synthesis of the C12−C24 fragment (lower part) of macrolactin A is described. The adapted strategy allowed building up the lower moiety by the assembly of three key intermediates via organometallic addition. One hydroxylic stereogenic center was introduced by the application of chiral sulfoxides methodology on fragment C19−C24. The preparation of the versatile 1,3-anti diol synthon C12−C16 was achieved via opening of chiral epoxide and subsequent oxidation to a hydroxy ketone. Finally, reductive elimination of the appropriate allylic dibenzoate with Na/Hg introduced directly the C16−C19 (E,E)-diene unit, in a highly efficient stereoselective fashion.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo049556l