Synthesis of novel polyyne analogues of sphingoid base via an iterative acetylene homologation sequence.
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.
Kim
Sanghee
S
College of Pharmacy, Seoul National University, San 56-1, Shilim, Kwanak, Seoul 151-742, Korea. pennkim@snu.ac.kr
Lee
Yun Mi
YM
Kang
Hee Ryong
HR
Cho
Jihee
J
Lee
Taeho
T
Kim
Deukjoon
D
D000114:Acetylene / Q000737:chemistry*; D015394:Molecular Structure; D053279:Polyynes / Q000138:chemical synthesis*; D013107:Sphingolipids / Q000737:chemistry*
D013107:Sphingolipids; D053279:Polyynes; D000114:Acetylene