CATALYTIC IRON-MEDIATED ENE CARBOCYCLIZATIONS OF TRIENES: ENANTIOSELECTIVE SYNTHESES OF THE IRIDOID MONOTERPENES (-)-MITSUGASHIWALACTONE AND (+)-ISOIRIDOMYRMECIN

Article abstract of DOI:10.1016/S0040-4039(00)74120-7

The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter.The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and (+)-Isoiridomyrmecin (2).