| Reference: | Smith, A. B. III; Beauchamp, T. J.; LaMarche, M. J.; Kaufman, M. D.; Qiu, Y.; Arimoto, H.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 2000, 122, 8654-8664 (Selected organometallic steps). DOI |
| Keywords: | CarboxAmide(Evans) -> CarboxAmide(Weinreb) • O-H -> O-SiMe2tBu • CarboxAmide(Weinreb) -> Aldehyde • Li/I -> Li-Alkyl • Li-Alkyl -> Zn-Alkyl • Wittig-iodomethyl • Wittig-alkyl -> Ene-cis • Aldol-B-Evans • Ti-Allyl+Aldehyde • Pd/Zn-Alkyl+Vinyl-X • Negishi coupling • Li-Allyl-P+Aldehyde • Aldehyde+Li-R • Li/H -> Li-Allyl-X • Alkyl-OH -> Alkyl-I • Alkyl-X -> Alkyl-Phosphonium • |
| Reagents: | BOTfBu2 • NMe(OMe)-AlMe2 • SiMe2tBu-OTf • AlHiBu2 • NaN(SiMe3)2 • BuLi(tert) • ZnCl2 • Alkyl-ZnX • Pd(PPh3)4 • BuLi(tert) • MeI • PPh3, I2 • PPh3 • NaN(SiMe3)2 • Allyl-PPh2 • PPh3=C(Me)-I • Ti(OiPr)4 • NEtiPr2 • |