Total synthesis of Radicicol:
| Reference: | Garbachio, R. M.; Stachel, S. J.; Baeschln, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908. DOI |
| Reactions: | Mitsunobu → OC(O)R • Alkyl-OH → Alkyl-OC(O)R • Alkyl-OH inversion • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • CompE+-Alkyl-X/Epoxide+M-R • Vilsmeier formylation • Aryl-H → Aryl-CHO • Friedel-Crafts Acylation • RCM → Lactone • Lactone-9+ • O-Me → O-H (phenol) • Aryl-H → Aryl-Cl • O-H → O-SiPh2tBu (phenol) • Pinnick oxidation • Aldehyde → CarboxAcid • O-H → O-SiMe2tBu (phenol) • CompE+-Alkyl-X/Epoxide+M-R • CompE+-Alkyl-X/CarboxEster+M-R • Sulfide → Sulfoxide • Ketal(thio) → Ketone • O-SiPh2tBu → O-H • O-C(O)R → O-H • |
| Reagents: | POCl3 • Benzyl-X • B(Br)3 • SiPh2tBu-Cl • Epoxide • PPh3, DIAD • Chlorite, sodium • SiMe2tBu-Cl • Perbenzoic acid, 3-chloro • Acetic anhydride, NEt3 • Bicarbonate, sodium • SO2Cl2 • Vilsmeier reagent • Grubbs I • DMF (react) • |