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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 • Si-Alkynyl → H-Alkynyl • O-SiMe2tBu → O-H • Mitsunobu → Cl • Alkyl-OH → Alkyl-Cl • Diimide+Alkyne • Peterson → Enyne • Li-Allenyl/Propargyl+Aldehyde • Aldehyde+Li-R • Si-Alkynyl+Acetal • Lactone-5 • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • RCM → Ring-Si • Pd/Si-Vinyl+Vinyl-X • Ether-9 • Hiyama coupling • Si-Alkynyl → I-Alkynyl • 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, R4N+ • SiMe2tBu-OTf • DDQ • Dess-Martin • Allenyl-Li • Fluoride, R4N+ • P(Oct)3 • Chiral auxiliary-Boronate • Diimide • Schrock cat •

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