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Total Synthesis of C30 Botryococcene and epi ‐Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes
Author(s) -
Cormier Morgan,
de la Torre Aurélien,
Marek Ilan
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808709
Subject(s) - stereocenter , enantioselective synthesis , epimer , total synthesis , stereochemistry , ring (chemistry) , chemistry , triterpene , organic chemistry , catalysis , medicine , alternative medicine , pathology
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.