Total synthesis of Pramanicin:
| Reference: | Barrett, A. G. M.; Head, J.; Smith, M. L.; Stock, N. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1999, 64, 6005. DOI |
| Reactions: | N-H → N-Boc • Selenide → Selenoxide • N-Boc → N-H • O-SiMe2tBu → O-H • Si-Alkyl → HO-Alkyl • HWE → EnoateEster • Selenoxide-Ei → EneLactam • Lactam → EneLactam • Sharpless epoxidation • Lactam → Lactam-α-SeR • Lactam-5 • Li-SiR3+EnoateAmide • Lactam enolate+Aldehyde • ConjAdd-Aldol • HWE → EnoateEster • Enone → Enone-α-OR • CarboxEster → Alkyl-OH • CarboxAcid → CarboxEster • EnoateEster → Allyl-OH • EnoateEster → Allyl-OH • Alkyl-OH → Aldehyde • Allyl-OH → Enone • Alkyl-OH → Aldehyde-α-OR • O-H → O-SiMe2tBu • |
| Reagents: | SOCl2 • BH4-Na+ • SiMe2tBu-Cl • Boc2O • LiNiPr2 • H2O2 • P(O)(OR)2CH2-C(O)OR' • Hydroperoxide, tbutyl - Ti • Epoxide • Dess-Martin • Acetic acid, trifluoro • H2SiF6 • SePh-Br • Ni(acac)2 • DMAP • Bifluoride, potassium • SiR3-Li • AlHiBu2 • Dess-Martin • P(O)(OR)2CH2-C(O)OR' • AlHiBu2 • Dess-Martin • Dioxirane • Tartrate, diisopropyl • Perbenzoic acid, 3-chloro • HOMe (react) • NaH • NaH • |