Total Synthesis of C30 Botryococcene and epi‐Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes. Issue 40 (11th September 2018)

• Record Type: Journal Article
• Authors: Cormier, Morgan; de la Torre, Aurélien; Marek, Ilan
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 40(2018)
• Page Start: 13237
• Page End: 13241
• Publication Date: 2018-09-11
• Subjects: botryococcene -- carbometalation -- cyclopropane -- organoalane -- ring-opening; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808709
• Languages: English
• ISSNs: 1433-7851

Abstract

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. Abstract : A novel approach was developed for the preparation of acyclic hydrocarbons bearing one quaternary and one tertiary stereocenter in a 1, 4‐relationship. The method is based on the diastereoselective biomimetic ring‐opening of cyclopropane methanol derivatives using ambiphilic organoalane nucleophiles. The strategy was applied to the total synthesis of botryococcene and epi ‐botryococcene.