Synthetic Progress toward Azadirachtins. 1. Enantio- and Diastereoselective Synthesis of the Left-Wing Fragment of 11-epi-Azadirachtin I

A highly enantio- and diastereoselective synthesis of the left-wing fragment of 11-epi-azadirachtin I characterized with the pairwise use of palladium- and gold-catalyzed cascade reactions is presented. By enlisting a sequence of stereocontrolled transformations, our 21-step route established the st...

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Bibliographic Details
Published in:Organic letters 2015-05, Vol.17 (10), p.2342-2345
Main Authors: Shi, Hang, Tan, Ceheng, Zhang, Weibin, Zhang, Zichun, Long, Rong, Luo, Tuoping, Yang, Zhen
Format: Article
Language:English
Subjects:
Limonins - chemical synthesis
Limonins - chemistry
Models, Molecular
Molecular Conformation
Stereoisomerism
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Summary:A highly enantio- and diastereoselective synthesis of the left-wing fragment of 11-epi-azadirachtin I characterized with the pairwise use of palladium- and gold-catalyzed cascade reactions is presented. By enlisting a sequence of stereocontrolled transformations, our 21-step route established the stereocenters of the left-wing fragment from one chiral starting material, (−)-carvone, which would significantly facilitate the synthetic studies of the azadirachtin-type limonoids.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00829