Total synthesis of Equisetin:
| Reference: | Burke, L T; Dixon, D J.; Ley, S. V.; Rodrigues, F. Org. Lett. 2000, 2, 3611. DOI |
| Reactions: | O-SiMe2tBu → O-H • Lactam-5 • HWE → Enone • HWE → Diene • Aldehyde → Alkyl-OH • N-H → N-C(O)R • CarboxEster(thio) → CarboxAmide • Ozonolysis • Diels-Alder, Intram, Ene • Bicyclo(440) • O-H → O-C(O)R • O-H → O-SiMe2tBu • O-C(O)R → O-H • Alkyl-OH → Aldehyde • O-SiMe2tBu → O-H • KetoAmide enolate+CarboxEster • Lactam-5 • Alkyl-OH → Aldehyde • |
| Reagents: | P(O)(OR)2CH2-Vinyl • BuLi(n) • Acetic anhydride, Py • O3 • SiMe2tBu-Cl • DMSO, (COCl)2 (Swern) • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • P(O)(OR)2CHR-C(O)R' • BuLi(n) • HF • NaH • AgOC(O)CF3 • BH4-Na+ • LiClO4 • Carbonate, potassium • NEt3 • |