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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
Keywords: ArylO-Me → ArylO-H • O-H → O-SiPh2tBu • Pinnick oxidation • Aldehyde → CarboxAcid • O-H → O-SiMe2tBu • O-SiPh2tBu → O-H • Ketal(thio) → Ketone • O-C(O)R → O-H • Aryl-H → Aryl-Cl • Mitsunobu → Ester • Alkyl-OH → Alkyl-OC(O)R • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Vilsmeier formylation • Aryl-H → Aryl-CHO • RCM → Lactone • Lactone-9+ • CompE+-Alkyl-Cl/Epoxide+Li-R • CompE+-Alkyl-X/CarboxEster+Li-R •
Reagents: POCl3 • B(Br)3 • SiPh2tBu-Cl • Epoxide • DIAD • Chlorite, sodium • SiMe2tBu-Cl • Perbenzoic acid, 3-chloro • Acetic anhydride, NEt3 • Bicarbonate, sodium • SO2Cl2 • DMF (react) • Vilsmeier reagent • Grubbs I •

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