title: Synthesis of iriomoteolide-1a C13-C23 fragment via asymmetric conjugate addition and Julia-Kocienski coupling reaction.
abstract: The key C13-C23 fragment toward the total synthesis of iriomoteolide-1a (1) has been constructed from an 1,2-acetonide containing aldehyde 5 via a Julia-Kocienski olefination with the C16-C23 segment 6. The key step involves stereoselective introduction of the C29 methyl group by a highly efficient CuI-Tol-BINAP-catalyzed asymmetric conjugate addition of methylmagnesium bromide to an alpha,beta-unsaturated ester.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
authors.forename: Yen-Jin
authors.initials: YJ
authors.lastname: Chin
authors.forename: Shun-Yi
authors.initials: SY
authors.lastname: Wang
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D004952:Esters; D018942:Macrolides; C520799:iriomoteolide-1a