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Updated: May 20, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Biomimetic Synthesis of Cucurbalsaminone A
Dattatraya H Dethe1, Chirantan Singha1, Salman A Siddiqui1
1Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208016, India.
Abstract:
Cucurbalsaminones, notable for their unique 5/6/3/6/5-fused pentacyclic triterpenoid structure, are potent inhibitors of P-glycoprotein. In this study, we propose a biosynthetic pathway starting from lanosterol, aiming to elucidate how these types of complex structures are synthesized by nature. Based on this, we present the first synthesis of cucurbalsaminone A in a biomimetic fashion. This synthesis emphasizes key steps including allylic oxidation/olefin isomerization, Lewis acid-mediated sequential migration of Me and H, and the oxa-di-π-methane rearrangement.
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