酸化的フェノールカップリングと分子内アザ-マイケル反応を基盤としたHasubananアルカロイド類の合成研究

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  • Synthetic Studies of Hasubanan Alkaloids Based on Oxidative Phenolic Coupling and Intramolecular Aza-Michael Reaction

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<p>Alkaloids with fused polycyclic skeletons are attractive targets for synthetic organic chemists due to their structural complexity and biological activity. Developing efficient synthetic strategies for these compounds is one of the key challenges in the field of synthetic research. When planning the synthesis of natural products with such complex three-dimensional structures, the key challenge is to introduce the appropriate functional group at the desired position while building the three-dimensional framework of the natural product. Various strategies and synthetic methodologies are needed to face these challenges. Herein, we disclose the synthesis of fused polycyclic alkaloids based on the dearomative oxidative phenolic coupling reaction of phenols followed by regioselective intramolecular aza-Michael reactions of dienones, allowing the efficient synthesis of a series of hasubanan alkaloids. In this study, three hasubanan alkaloids ((−)-Metaphanine, (+)-Stephadiamine, and Cepharatines) were synthesized by the late diversification of their C and D ring moieties based on regioselective aza-Michael reaction of dienones obtained by dearomative oxidative phenolic coupling reaction of phenols. The synthesis of (−)-metaphanine was achieved through an efficient construction of the Hasubanan skeleton by utilizing the regioselective aza-Michael reaction at C14. (+)-Stephadiamine was synthesized employing an aza-benzylic acid-type rearrangement reaction to contraction of C ring. Additionally, cepharatines were successfully synthesized through the reorganization of the D ring, which involved a cascade reaction featuring a retro aza-Michael reaction and subsequent aminal formation.</p>

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