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

Morgan Cormier; Aurelien de la Torre; Ilan Marek

doi:10.1002/anie.201808709

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

Morgan Cormier, Aurelien de la Torre, Ilan Marek

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	13237-13241
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	40
DOIs	https://doi.org/10.1002/anie.201808709
State	Published - 1 Oct 2018

Keywords

botryococcene
carbometalation
cyclopropane
organoalane
ring-opening

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry

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10.1002/anie.201808709

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title = "Total Synthesis of C30 Botryococcene and epi-Botryococcene by a Diastereoselective Ring Opening of Alkenylcyclopropanes",

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.",

keywords = "botryococcene, carbometalation, cyclopropane, organoalane, ring-opening",

author = "Morgan Cormier and \{de la Torre\}, Aurelien and Ilan Marek",

note = "Publisher Copyright: {\textcopyright} 2018 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

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doi = "10.1002/anie.201808709",

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AU - Cormier, Morgan

AU - de la Torre, Aurelien

AU - Marek, Ilan

PY - 2018/10/1

Y1 - 2018/10/1

N2 - 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.

AB - 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.

KW - botryococcene

KW - carbometalation

KW - cyclopropane

KW - organoalane

KW - ring-opening

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U2 - 10.1002/anie.201808709

DO - 10.1002/anie.201808709

M3 - مقالة

SN - 1433-7851

VL - 57

SP - 13237

EP - 13241

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -

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

Abstract

Keywords

All Science Journal Classification (ASJC) codes

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