title: Total synthesis of dermostatin A.
abstract: The concise total synthesis of dermostatin A is described. Highlights include a two-directional application of the asymmetric acetate aldol method developed in our lab, a novel diastereotopic-group-selective acetal isomerization for terminus differentiation, and a selective cross-metathesis reaction between a terminal olefin and a trienal. A study of the scope and viability of similar cross-metathesis reactions is also described. The synthesis is convergent and utilizes fragments of roughly equal complexity.
authors.affiliation: Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215, United States.
authors.forename: Yingchao
authors.initials: Y
authors.lastname: Zhang
authors.forename: Carolynn C
authors.initials: CC
authors.lastname: Arpin
authors.forename: Aaron J
authors.initials: AJ
authors.lastname: Cullen
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Mitton-Fry
authors.forename: Tarek
authors.initials: T
authors.lastname: Sammakia
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D011090:Polyenes; D011108:Polymers; C024617:polyol; C030347:dermostatin A