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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Asymmetric Total Synthesis of Inthomycins A, B, and C
Jae Hyun Kim1, Yeonghun Song1, Min Jung Kim1
1College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea.
Abstract:
Herein, we report the asymmetric total syntheses of inthomycin antibiotics containing a methylene-interrupted oxazolyl-triene motif. Utilizing the α,β-unsaturated aldehyde as a common intermediate, all three inthomycins A-C were divergently synthesized. The asymmetric ynone reduction provided an R-configured secondary alcohol as in the natural products with high enantioselectivity. The geometrically different triene units for each inthomycin were stereoselectively established via methyl cuprate conjugate addition, isomerization of the α,β-unsaturated aldehyde intermediate, and stereoretentive cross-coupling reactions.
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