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Updated: Nov 9, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Unified Total Syntheses of (±)-Sessilifoliamides B, C, and D
Wesley J Olivier1, Alex C Bissember1, Jason A Smith1
1School of Natural Sciences - Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia.
Abstract:
The 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.
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