title: Enantioselective synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a.
abstract: Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.
authors.affiliation: Kenan, Caudill, Venable and Murray Laboratories of Chemistry, University of North Carolina at Chapel Hill , Chapel Hill, North Carolina 27599, United States. crimmins@email.unc.edu
authors.forename: Michael T
authors.initials: MT
authors.lastname: Crimmins
authors.forename: Anne-Marie R
authors.initials: AM
authors.lastname: Dechert
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D053778:Thiazolidines / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D018942:Macrolides; D053778:Thiazolidines; C520799:iriomoteolide-1a; C033089:thiazoline-2-thione; C116609:3-hydroxybutanal