Formal Synthesis of (±)-Coriolin by Diastereocontrolled Nickel(0)-Catalyzed 'Metallo-ene-type' Cyclization/Methoxycarbonylation

Von Oppolzer, Wolfgang; Ando, Akira

doi:10.2533/chimia.1992.122

Scientific article

English

Formal Synthesis of (±)-Coriolin by Diastereocontrolled Nickel(0)-Catalyzed 'Metallo-ene-type' Cyclization/Methoxycarbonylation

ContributorsVon Oppolzer, Wolfgang; Ando, Akira

Published inChimia, vol. 46, no. 4, p. 122-125

Publication date1992

Abstract

Bicyclooctanone (±)-2, an advanced intermediate for the synthesis of (±)-coriolin, has been synthesized in ten steps starting from 2,2-dimethylpent-4-enal (7). The key step 6 → 3 + 11 is a highly diastereoselective, Ni0-catalyzed, tandem intramolecular alkene allylation/carbonylation reaction.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

VON OPPOLZER, Wolfgang, ANDO, Akira. Formal Synthesis of (±)-Coriolin by Diastereocontrolled Nickel(0)-Catalyzed “Metallo-ene-type” Cyclization/Methoxycarbonylation. In: Chimia, 1992, vol. 46, n° 4, p. 122–125. doi: 10.2533/chimia.1992.122

Article (Published version)

CC BY-NC

Identifiers

PID : unige:152416
DOI : 10.2533/chimia.1992.122

Journal ISSN0009-4293

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Formal Synthesis of (±)-Coriolin by Diastereocontrolled Nickel(0)-Catalyzed 'Metallo-ene-type' Cyclization/Methoxycarbonylation

Bicyclooctanone (±)-2, an advanced intermediate for the synthesis of (±)-coriolin, has been synthesized in ten steps starting from 2,2-dimethylpent-4-enal (7). The key step 6 → 3 + 11 is a highly diastereoselective, Ni0-catalyzed, tandem intramolecular alkene allylation/carbonylation reaction.

Technical informations