Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction

Araki, Yasunori; Miyoshi, Natsumi; Morimoto, Kazuki; Kudoh, Takayuki; Mizoguchi, Haruki; Sakakura, Akira

doi:10.1021/acs.joc.9b02811

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2024

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Cited by 6 publications

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Domino Reactions through Recursive Anionic Cascades: The Advantageous Use of Nitronates

2022

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Recursive Anionic Cyclization (RAC) continues to proliferate as a mechanistically distinct domino strategy. Deployment of nitroalkanes as a source of recursive carbanions has created a niche operating space for generating molecular complexity and diversity. This new corollary i. e. recursive nitronate cyclization is the basis of a domino [5 C+1 C] cyclization strategy wherein nitroalkanes act as one‐carbon lynchpin, providing rapid access to topologically intriguing, densely functionalized carbo‐ and heterocycles embodying multiple chiral centers with regio‐, stereo‐ and enantioselectivity. Extension to aromatic domains, particularly via benzannulation reactions, has further consolidated the operating space. While leveraging the functional versatility of nitro group for post‐domino modifications, such endeavors have culminated in total synthesis of diverse natural products. An incisive analysis of recursive nitronate cyclizations and their emergent potentials is delineated in this review. It is hoped that this focused narrative will enthuse and draw new practitioners to the arena to advance the field.

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