Total synthesis of Discodermolide (Part 1):
| 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. DOI |
| Reactions: | Li/I → Li-Alkyl • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • CarboxAmide(Evans) → CarboxAmide(Weinreb) • Li-R → Zn-R • Wittig-iodomethyl • Pd/Zn-Alkyl+Vinyl-X • Aldol-B-Evans • CarboxAmide enolate+Aldehyde (asym) • CarboxAmide(Weinreb) → Aldehyde • O-H → O-PMB • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • O-H → O-SiMe2tBu • CarboxAmide(Weinreb) → Aldehyde • CarboxAmide(Weinreb) → Alkyl-OH • Alkyl-OH → Alkyl-I • O-PMB → O-H • O-H → O-CPh3 • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • |
| Reagents: | Chiral auxiliary (amide-Evans) • B(OTf)Bu2 • NMe(OMe)-AlMe2 • BuLi(tert) • ZnCl2 • Alkyl-ZnX • Chiral auxiliary (amide-Evans) • AlH4-Li+ • DMSO, (COCl)2 (Swern) • NEt3 • DDQ • AlH4-Li+ • Chiral auxiliary (amide-Evans) • B(OTf)Bu2 • BH4-Li+ • I2 • SiMe2tBu-OTf • AlHiBu2 • NaN(SiMe3)2 • PPh3=CI(Me) • Pd(PPh3)4 • DDQ • Ph3CCl • DMAP • AlHiBu2 • Dess-Martin • Chiral auxiliary (amide-Evans) • PMBO-C(=NH)-CCl3 • Vinyl-I • |