| 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 |