-rychnovsky.gif)
Total synthesis of Roflamycoin (Part 2):
| Reference: | Rychnovsky, S. D.; Khire, U. R.; Yang, G. J. Am. Chem. Soc. 1997, 119, 2058. DOI (Part 3) (Part 1) |
| Reactions: | O-SiMe2tBu → O-H • Alkyl-OH → Alkyl-I • Alkyl-C≡N → Alkyl-H • Nitrile anion+Alkyl-X • EnolEther → Enal • Lactone-9+ • HWE → EnoateEster (intram) • Diol-1,2 cleavage • Li-R → Mg-R • Aldehyde+Mg-Vinyl • Mg-Vinyl+Aldehyde • CompE+-Aldehyde/CarboxEster+M-R • Ketal → Diol-1,2 • O-Bn → O-H • CarboxAcid → CarboxEster • Alkyl-OH → Aldehyde • Li/Sn → Li-Vinyl • Li-R → Mg-R • Nitrile anion+Alkyl-X • |
| Reagents: | LiNEt2 • DMPU (solvent) • Fluoride, R4N+ • PPh3, I2 • LiNEt2 • DMPU (solvent) • Li°/NH3 • BOP • Dess-Martin • Sulfonyl chloride, methane, NEt3 • P(O)(OR)2CHR-C(O)OR' • DBU • Dowex • Periodate, sodium • LiCH2-CN • Butadiene, 1-SnR3 • Butadiene, 1-OR • BuLi(n) • MgBr2 • P(O)(OR)2CHR-C(O)OR' • |