Stereoselective Total Synthesis of Axially Chiral Natural Products via Biaryl Lactones

Axially chiral natural products are rewarding synthetic targets, due to their wide distribution, diverse structures, and promising bioactivities. The “lactone concept” provides an efficient strategy for the regio- and stereoselective construction of even bulky biaryls. Key steps are the intramolecul...

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Bibliographic Details
Published in:Accounts of chemical research 2001-08, Vol.34 (8), p.615-624
Main Authors: Bringmann, Gerhard, Menche, Dirk
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Biological Products - chemistry
Indicators and Reagents
Lactones - chemical synthesis
Stereoisomerism
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Summary:Axially chiral natural products are rewarding synthetic targets, due to their wide distribution, diverse structures, and promising bioactivities. The “lactone concept” provides an efficient strategy for the regio- and stereoselective construction of even bulky biaryls. Key steps are the intramolecular coupling of the ester-prefixed molecular portions to give (mostly configurationally unstable) biaryl lactones and their stereoselective ring cleavage (usually by dynamic kinetic resolution), leading to the one oroptionallythe other atropisomeric product from the same lactone. Stereoisomeric byproducts can be recycled by recyclization back to the lactone. The broad applicability of the method is demonstrated in the total synthesis of selected representatives from five very different classes of natural biaryl products.
ISSN:0001-4842
1520-4898
DOI:10.1021/ar000106z