Synthesis of a Functionalized Bicyclo[3.2.1]Octane: A Common Subunit to Kauranes, Grayananes, and Gibberellanes.

Authors

Nicolas Fay, Camil Benbouziyane, Cyrille Kouklovsky, Aurélien de la Torre

Published in

Chemistry (Weinheim an der Bergstrasse, Germany). Pages e02441. Sep 13, 2025. Epub Sep 13, 2025.

Abstract

Kauranes, grayananes, and gibberellanes are three important diterpenoid families. These natural products all share a bicyclo[3.2.1]octane skeleton, with oxidation at very specific positions. In this manuscript, we describe the synthesis of a bicyclo[3.2.1]octane building block, which could serve as a potential intermediate for the synthesis of natural products from these three families. A first approach relying on a 1,4-sila-Prins cyclization was first explored, which required the selective functionalization of dihydrocarvone (via C─H activation and selective oxidation). This strategy resulted in a dead end when a 1,2-cyclization product was obtained. An alternative strategy relying on ring-closing metathesis (RCM) allowed to successfully achieve the synthesis of the desired scaffold in 8 steps from cyclohexenone.

PMID:
40944365
Bibliographic data and abstract were imported from PubMed on 13 Sep 2025.

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