Total Synthesis of C30 Botryococcene and Epi-Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2018 Aug 23

PMID 30134044

Citations 5

Authors

Morgan Cormier

Aurelien de la Torre

Ilan Marek

Affiliations

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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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