title: Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade.
abstract: The mechanism of the cascade oxidative dearomatization-transannular Diels Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene.
authors.affiliation: Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, USA.
authors.forename: Alessandra
authors.initials: A
authors.lastname: Polara
authors.forename: Silas P
authors.initials: SP
authors.lastname: Cook
authors.forename: Samuel J
authors.initials: SJ
authors.lastname: Danishefsky