Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 4, Pages 1174-1177Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201812822
Keywords
asymmetric synthesis; goniomitine; indole alkaloids; natural products; total synthesis
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Funding
- National Natural Science Foundation of China [21325207, 21532003, 21871152, 21790330]
- 111 project [B06005]
- Ministry of Education of China
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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.
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