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Scalable Enantioselective Total Synthesis of (−)‐Goniomitine
Author(s) -
Bin HuaiYu,
Wang Ke,
Yang Dan,
Yang XiaoHui,
Xie JianHua,
Zhou QiLin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201812822
Subject(s) - enantioselective synthesis , ketone , asymmetric hydrogenation , yield (engineering) , total synthesis , chemistry , combinatorial chemistry , iridium , noyori asymmetric hydrogenation , enone , catalysis , organic chemistry , materials science , metallurgy
A scalable enantioselective total synthesis of (−)‐goniomitine has been developed by using an iridium‐catalyzed asymmetric hydrogenation of an exocyclic enone ester to control the configuration of the molecule. The synthesis begins from commercially available starting materials, and proceeds through an integrated asymmetric ketone hydrogenation, Johnson–Claisen rearrangement, and one‐pot oxidation/deprotection/cyclization process. With this highly efficient and scalable strategy, (−)‐goniomitine was synthesized in eleven steps with 27 % overall yield, and formal enantioselective syntheses of (+)‐1,2‐dehydroaspidospermidine, (+)‐aspidospermidine, and (+)‐vincadifformine were also achieved.