Total Synthesis of C30 Botryococcene and epi‐Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes |
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| Authors: | Morgan Cormier Aurélien de la Torre Ilan Marek |
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| Affiliation: | Technion—Israel Institute of Technology, Schulich Faculty of Chemistry, Haifa, Israel |
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| Abstract: | Trialkylaluminum compounds perform a diastereoselective 1,6‐ring fragmentation of alkenylcyclopropane. This new tool allows the preparation of hydrocarbon compounds containing two distant stereocenters with a good diastereocontrol. Inspired by the biosynthesis of botryococcene this methodology was applied successfully to the diastereo‐ and enantioselective preparation of this triterpene and its epimer. |
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| Keywords: | botryococcene carbometalation cyclopropane organoalane ring-opening |
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