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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-X • Ether-9 • Si-Alkynyl+Alkynyl-I • CarboxAcid -> Alkyl-OH •
Reagents: BF3·OEt2 • BH3·THF • SiMe2tBu-Cl • Alkynyl-SiR3 • TiCl4 • TsOH • Alkynyl-SiR3 • NIS • Acetic acid • 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 •

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