Enantioselective total synthesis of bistramide A.
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.
Crimmins
Michael T
MT
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
DeBaillie
Amy C
AC
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
D000081:Acetamides; D011714:Pyrans; D013141:Spiro Compounds; C059975:bistratene A