{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Gung BW"],"funding":["NIGMS NIH HHS"],"pagination":["4790-4795"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC3601937"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["2008(28)"],"pubmed_abstract":["Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C<sub>2</sub> 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."],"journal":["European journal of organic chemistry"],"pubmed_title":["First 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."],"pmcid":["PMC3601937"],"funding_grant_id":["R15 GM069441"],"pubmed_authors":["Gung BW","Omollo AO"],"additional_accession":[]},"is_claimable":false,"name":"First 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.","description":"Dideoxypetrosynol A is a C30 polyacetylenic alcohol with C<sub>2</sub> 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.","dates":{"release":"2008-01-01T00:00:00Z","publication":"2008 Oct","modification":"2025-04-04T01:26:31.976Z","creation":"2019-03-27T01:06:18Z"},"accession":"S-EPMC3601937","cross_references":{"pubmed":["23519828"],"doi":["10.1002/ejoc.200800593"]}}