Reference: | Garbachio, R. M.; Stachel, S. J.; Baeschln, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908. DOI |
Keywords: | Mitsunobu → Ester 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 Pinnick oxidation Aldehyde → CarboxAcid O-H → O-SiMe2tBu CompE+-Alkyl-X/Epoxide+Li-R CompE+-Alkyl-X/CarboxEster+Li-R Sulfide → Sulfoxide Ketal(thio) → Ketone O-SiPh2tBu → O-H O-C(O)R → O-H |
Reagents: | POCl3 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) |