image

Total synthesis of Brasilenyne:
Reference: Denmark, S.; Yang, S. M. J. Am. Chem. Soc. 2004, 126, 12432. DOI
Keywords: Lactone-5 --- O-H -> O-PMB --- CarboxAmide(Weinreb) -> Aldehyde --- O-H -> O-SiMe2tBu --- O-PMB -> O-H --- Alkyl-OH -> Aldehyde --- H/Si -> Alkyne --- O-SiMe2tBu -> O-H --- Mitsunobu -> Cl --- Alkyl-OH -> Alkyl-Cl(2°) --- Diimide+Alkynyl-I --- Peterson -> Enyne --- Li-Propargyl+Aldehyde --- Si-Alkynyl+Acetal --- B-Allyl-Ipc+Aldehyde --- RCM -> Ring-Si --- Pd/Si-Vinyl+Vinyl-I --- Ether-9 --- Si-Alkynyl+Alkynyl-I --- CarboxAcid -> Alkyl-OH
Reagents: BF3·OEt2 --- BH3·THF --- SiMe2tBu-Cl --- Alkynyl-SiR3 --- TiCl4 --- TsOH --- Alkynyl-SiR3 --- NIS --- AcOH --- NMe(OMe)-AlMe2 --- Ag2O --- AlHiBu2 --- Allyl-B(Ipc)2 --- BF3 --- BF3 --- NEt3 --- Schrock cat --- PdCl(Allyl) --- Fluoride, Bu4N+ --- SiMe2tBu-OTf --- DDQ --- Dess-Martin --- Allenyl-Li --- Fluoride, Bu4N+ --- P(Oct)3 --- Diimide --- Schrock cat

Syntheses Home