Open AccessFormal Synthesis of (±)-Coriolin by Diastereocontrolled Nickel(0)-Catalyzed 'Metallo-ene-type' Cyclization/Methoxycarbonylation
Author(s) -
Wolfgang Oppolzer,
Akira Andõ
Publication year - 1992
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1992.122
Subject(s) - carbonylation , ene reaction , tandem , catalysis , alkene , intramolecular force , nickel , chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , materials science , carbon monoxide , composite material
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.