title: Enantioselective total synthesis of bistramide A.
abstract: The enantioselective synthesis of bistramide A has been achieved with a longest linear sequence of 18 steps. The synthetic strategy involves the use of a distereoselective glycolate alkylation, an aldol addition of a chlorotitanium enolate of N-acylthiazolidinthione, and a Sharpless asymmetric epoxidation to synthesize the three key fragments.
authors.affiliation: Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA. crimmins@email.unc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Amy C
authors.initials: AC
authors.lastname: DeBaillie
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry
chemical_list: D000081:Acetamides; D011714:Pyrans; D013141:Spiro Compounds; C059975:bistratene A