Total synthesis of Waol A:
| Reference: | Gao, X.; Nakadai, M.; Snider, B. Org. Lett. 2003, 5, 451. DOI |
| Reactions: | O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Lactone-5 • Lactone enolate+Aldehyde • Aldol-Li → Aldol • Iodoetherification • Ether-6 • Epoxide → Allyl-OH • Reformatsky • Aldehyde → Cyanohydrin • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • CarboxEster enolate+Nitrile • Iodohydrin → Epoxide • |
| Reagents: | Cyanide, sodium • SiPh2tBu-Cl • BH4-Na+ • Fluoride, R4N+ • HCl • AgPF6 • I2 • LiNiPr2 • NEt3 • Crotonaldehyde • Imidazole • Bromoacetate • Zn° • SiMe3-Cl • |