title: A new, iterative strategy for the synthesis of unsymmetrical polyynes: application to the total synthesis of 15,16-dihydrominquartynoic acid.
abstract: [reaction: see text] A new iterative strategy for the synthesis of unsymmetrically substituted polyynes has been developed. The starting bromoalkyne is homologated by one acetylene unit through palladium-catalyzed cross-coupling with a TIPS-protected terminal acetylene and a subsequent in situ one-pot AgF-mediated desilylative bromination. The utility of this new synthetic method is demonstrated by its application to the total synthesis of (S)-(E)-15,16-dihydrominquartynoic acid.
authors.affiliation: College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
authors.forename: Shinae
authors.initials: S
authors.lastname: Kim
authors.forename: Taeho
authors.initials: T
authors.lastname: Lee
authors.forename: Hyojin
authors.initials: H
authors.lastname: Ko
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D053279:Polyynes
chemical_list: D000480:Alkynes; D005231:Fatty Acids, Unsaturated; D007202:Indicators and Reagents; C417933:minquartynoic acid; D053279:Polyynes