ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
Synthesis of a Functionalized Bicyclo[3.2.1]Octane: A Common Subunit to Kauranes, Grayananes, and Gibberellanes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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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.
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