title: Synthesis of novel polyyne analogues of sphingoid base via an iterative acetylene homologation sequence.
abstract: The first syntheses of polyyne-containing sphingoid base analogues were achieved by employing our iterative strategy that uses a two-step acetylene homologation sequence. In this process, a bromoalkyne is homologated by one acetylene unit through a Pd-catalyzed cross-coupling with a TIPS-protected acetylene and a subsequent in situ AgF-mediated desilylative bromination. Repeating this homologation sequence followed by cross-coupling with the long-chained terminal acetylene provides access to the polyyne framework in good overall yields.
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: Yun Mi
authors.initials: YM
authors.lastname: Lee
authors.forename: Hee Ryong
authors.initials: HR
authors.lastname: Kang
authors.forename: Jihee
authors.initials: J
authors.lastname: Cho
authors.forename: Taeho
authors.initials: T
authors.lastname: Lee
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D015394:Molecular Structure; D053279:Polyynes / Q000138:chemical synthesis*; D013107:Sphingolipids / Q000737:chemistry*
chemical_list: D013107:Sphingolipids; D053279:Polyynes; D000114:Acetylene