Enantioselective total synthesis of spirofungins A and B.
The enantioselective total synthesis of spirofungins A (1) and B (2) is reported in 14 steps over the longest linear sequence. Key steps include the use of thiazolidinethione-mediated aldol reactions to assemble the major fragments and installation of the C1-C6 side chain using a cross metathesis reaction.
Crimmins
Michael T
MT
Kenan and Caudill Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States. crimmins@email.unc.edu
O'Bryan
Elizabeth A
EA
D000447:Aldehydes / Q000138:chemical synthesis; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis; D011714:Pyrans / Q000138:chemical synthesis*; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D020005:Propanols; D011714:Pyrans; D013141:Spiro Compounds; C114877:spirofungin A; C493365:spirofungin B; C006463:allyl alcohol