Synthetic Progress toward Azadirachtins. 1. Enantio- and Diastereoselective Synthesis of the Left-Wing Fragment of 11-epi-Azadirachtin I
journal contributionposted on 15.05.2015 by Hang Shi, Ceheng Tan, Weibin Zhang, Zichun Zhang, Rong Long, Tuoping Luo, Zhen Yang
Any type of content formally published in an academic journal, usually following a peer-review process.
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.