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Unified total syntheses of (±)-sessilifoliamides B, C, and D
journal contribution
posted on 2023-05-20, 23:14 authored by Wesley OlivierWesley Olivier, Alexander BissemberAlexander Bissember, Jason SmithJason SmithThe first total syntheses of the Stemona alkaloids sessilifoliamides B and D and the second synthesis of sessilifoliamide C have been completed from a simple pyrrole substrate. The bicyclic lactam core was prepared on a gram scale via a Brønsted acid mediated cyclization and controlled oxidation with Dess–Martin periodinane. This delivered sessilifoliamide C (and its C-11 epimer) in 24% yield over 11 steps, and sessilifoliamides B and D in 13 and 17 steps, respectively.
History
Publication title
Organic LettersVolume
23Issue
9Pagination
3437-3441ISSN
1523-7060Department/School
School of Natural SciencesPublisher
Amer Chemical SocPlace of publication
1155 16Th St, Nw, Washington, USA, Dc, 20036Rights statement
Copyright 2021 American Chemical SocietyRepository Status
- Restricted