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Construction of the tetracyclic ring system of diterpene alkaloids via cationic [5 + 2] cycloaddition†
Kosuke Mizuno,Yoshitake Nishiyama,Satoshi Yokoshima
Organic & Biomolecular Chemistry Pub Date : 05/16/2023 00:00:00 , DOI:10.1039/D3OB00647F
Abstract

The ABCD ring system of C18/C19 diterpene alkaloids was constructed via cationic [5 + 2] cycloaddition to forge a bicyclo[3.2.1]octane, an intramolecular aldol reaction to form a seven-membered ring, oxidation of a phenol at the para-position, and introduction of a one-carbon unit via Stille coupling followed by oxidative cleavage of a furan ring.

Graphical abstract: Construction of the tetracyclic ring system of diterpene alkaloids via cationic [5 + 2] cycloaddition
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