title: Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected Diols.
abstract: Using stereo- and site-selective C-H allylation and crotylation of unprotected diols, an intermediate in the synthesis of premisakinolide A (bistheonellic acid B) that was previously made in 16-27 (LLS) steps is now prepared in only nine steps. This fragment also represents a synthesis of C(19)-C(32) of the actin-binding macrodiolide swinholide A.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Inji
authors.initials: I
authors.lastname: Shin
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin , Austin, Texas 78712, United States.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000199:Actins / Q000378:metabolism; D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008387:Marine Toxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000199:Actins; D000438:Alcohols; D018942:Macrolides; D008387:Marine Toxins; C509581:premisakinolide A; C086235:swinholide A