title: First Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the "Skipped" (Z)-Enediyne Moiety by Oxidative Coupling of Homopropargyl Phosphonium Ylide.
abstract: Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C2symmetry. The first total synthesis of both enantiomers of the potent anti-cancer natural product (+)- and (-)-dideoxypetrosynol A is reported. The key step is an oxidative coupling of a homopropargyl phosphonium ylide to prepare the "skipped" (Z)-enediyne moiety. The natural dideoxypetrosynol A was isolated as a racemic mixture as shown in structure1. The absolute configurations of the chiral centers are established for the (+)- and (-)-enantiomers using Burgess' enzymatic resolution procedure withPseudomonasAK lipase.
authors.affiliation: Department of Chemistry & Biochemistry, Miami University, Oxford, OH 45056.
authors.forename: Benjamin W
authors.initials: BW
authors.lastname: Gung
authors.forename: Ann O
authors.initials: AO
authors.lastname: Omollo
keywords: (Z)-enediyne; Total synthesis; anticancer; natural product