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

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posted on 15.05.2015, 00:00 by Hang Shi, Ceheng Tan, Weibin Zhang, Zichun Zhang, Rong Long, Tuoping Luo, Zhen Yang
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.