biostudies-literatureGung BWNIGMS NIH HHS4790-4795https://www.ebi.ac.uk/biostudies/studies/S-EPMC3601937biostudies-literatureUnknown2008(28)Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C₂ symmetry. 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" (<i>Z</i>)-enediyne moiety. The natural dideoxypetrosynol A was isolated as a racemic mixture as shown in structure <b>1</b>. The absolute configurations of the chiral centers are established for the (+)- and (-)-enantiomers using Burgess' enzymatic resolution procedure with <i>Pseudomonas</i> AK lipase.European journal of organic chemistryFirst Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the "Skipped" (<i>Z</i>)-Enediyne Moiety by Oxidative Coupling of Homopropargyl Phosphonium Ylide.PMC3601937R15 GM069441Gung BWOmollo AOfalseFirst Total Synthesis of the Potent Anticancer Natural Product Dideoxypetrosynol A: Preparation of the "Skipped" (<i>Z</i>)-Enediyne Moiety by Oxidative Coupling of Homopropargyl Phosphonium Ylide.Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C₂ symmetry. 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" (<i>Z</i>)-enediyne moiety. The natural dideoxypetrosynol A was isolated as a racemic mixture as shown in structure <b>1</b>. The absolute configurations of the chiral centers are established for the (+)- and (-)-enantiomers using Burgess' enzymatic resolution procedure with <i>Pseudomonas</i> AK lipase.2008-01-01T00:00:00Z2008 Oct2025-04-04T01:26:31.976Z2019-03-27T01:06:18ZS-EPMC36019372351982810.1002/ejoc.200800593