Studies Directed toward the Synthesis of Terreulactone A:  Rapid Construction of the A, B, C Rings

An efficient, rapid synthesis of the A, B, C rings of terreulactone A is described. Key steps in the synthesis include a diastereoselective benzylic acid rearrangement to create the desired quaternary center at C2 and a mild bromolactonization to assemble the lactonic ring A.

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Bibliographic Details
Published in:Organic letters 2006-02, Vol.8 (3), p.423-425
Main Authors: Liu, Haibo, Siegel, Dionicio R, Danishefsky, Samuel J
Format: Article
Language:English
Subjects:
Aspergillus - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Cyclization
Molecular Structure
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
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Description
Summary:An efficient, rapid synthesis of the A, B, C rings of terreulactone A is described. Key steps in the synthesis include a diastereoselective benzylic acid rearrangement to create the desired quaternary center at C2 and a mild bromolactonization to assemble the lactonic ring A.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052618p