title: A Total Synthesis of FK-506(1).
abstract: A total synthesis of FK-506 (1) is presented. The synthesis features a highly convergent approach utilizing a block coupling strategy. Top and bottom half sections of the molecule are coupled by addition of a vinyl cuprate with a spiroenone. The alpha-allyl aldol functionality is revealed by a reductive opening of the spiroenone system. The labile alpha,beta-diketoamide hemiketal portion of the molecule is prepared by a late stage generation and oxidation of a masked enediol. Top and bottom half segments are themselves derived by coupling of smaller subunits, resulting in a very convergent route.
authors.affiliation: Department of Chemistry, McCormick Road, University of Virginia, Charlottesville, Virginia 22901.
authors.forename: Robert E.
authors.initials: RE
authors.lastname: Ireland
authors.forename: James L.
authors.initials: JL
authors.lastname: Gleason
authors.forename: Laura D.
authors.initials: LD
authors.lastname: Gegnas
authors.forename: Thomas K.
authors.initials: TK
authors.lastname: Highsmith