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Updated: Jun 16, 2026

Culturing and Measuring Fetal and Newborn Murine Long Bones
Published on: April 26, 2019
Enantiospecific synthesis of the cubitane skeleton
Elisabeth Schöttner1, Maren Wiechoczek, Peter G Jones
1TU Braunschweig, Institutes of Organic, Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany.
Abstract:
The fully substituted 12-membered macrocycle of the cubitane-type diterpenoids has been assembled in an enantioselective manner following a novel "bridge-and-cut" strategy. Hydroxyalkylation of (S)-carvone afforded a carvonylgeraniol, which underwent transannular cyclization on treatment with samarium diiodide in THF. Fragmentation of one of the shorter bridges of the resulting [8.2.2]bicycle liberated the 12-membered ring with the desired cis-arrangement of the isopropenyl side chains.
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