title: Enantioselective synthesis of apoptolidinone: exploiting the versatility of thiazolidinethione chiral auxiliaries.
abstract: An efficient, enantioselective synthesis of apoptolidinone has been completed, demonstrating the versatility of thiazolidinethione auxiliaries. Three propionate aldol additions and two asymmetric glycolate alkylations function to establish 8 of the 12 stereogenic carbon centers. A cross-metathesis reaction is utilized to assemble the C1-C10 trieneoate fragment and the C11-C28 polypropionate region of the molecule.
authors.affiliation: Department 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: Hamish S
authors.initials: HS
authors.lastname: Christie
authors.forename: Kleem
authors.initials: K
authors.lastname: Chaudhary
authors.forename: Alan
authors.initials: A
authors.lastname: Long
mesh_terms: D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*; D053778:Thiazolidines
chemical_list: D018942:Macrolides; D011753:Pyrones; D013844:Thiazoles; D053778:Thiazolidines; C506738:apoptolidin A; C504948:apoptolidinone; C033089:thiazoline-2-thione