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Updated: Jun 12, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Formal Synthesis of Amipurimycin and 4'-Deoxymiharamycin B by Way of Sequential Asymmetric Metal Catalysis
Donghoon Park1, Young Ho Rhee1
1Department of Chemistry, Pohang University of Science and Technology, 77 Cheongam-Ro, Pohang, Kyungbuk 37673, Republic of Korea.
Abstract:
Herein, we describe a highly efficient formal synthesis of nucleoside antibiotics amipurimycin and 4'-deoxymiharamycin B. A signature event is highlighted by the sequential metal catalysis combining (i) Pd-catalyzed asymmetric hydroalkoxylation of an alkoxyallene; (ii) Ru-catalyzed enyne-methathesis, and (iii) Os-catalyzed dihydroxylation. Remarkably, this atom-efficient sequence allows for the construction of a 3'-branched pyranose core structure in only four steps from readily available Garner's aldehyde.
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