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Total synthesis of Discodermolide (partial):
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+Aldehyde • Aldehyde+Li-R • Li/H → Li-Allyl-X • High pressure • 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-Li • PPh3=CI(Me) • Ti(OiPr)4 • NEtiPr2

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