Synthesis of Deoxyaspidodispermine Based on a Functional Protecting Group Strategy. 2022

Kouassi Signo, and Sylvain Canesi
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal H3C 3P8, Québec, Canada.

A synthesis of deoxyaspidodispermine was produced from homotyramine. This approach is based on the application of a functional protecting group strategy that not only masks the reactivity of sensitive groups during crucial steps but also possesses a moiety desired in the final target, which is transferred to the substrate at the time of deprotection. This synthesis highlights an aza-Michael-Smiles ring-closure cascade, which enables the formation of a tetracyclic system from a nosylamide protecting group.

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