Reference: | Chu-Moyer, M. Y.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1994, 116, 11213. DOI |
Keywords: | Enone → Allyl-OH Diol-1,2 cleavage Lactone-5 O-SiMe2tBu → O-H Aldehyde → Alkyl-OH O-H → O-SiMe2tBu Allyl-OH → Enone O-SiMe2tBu → O-H Mechanism CompE+-Aldehyde/CarboxEster+Wittig Lactone → Lactol CompRed-Lactone/Lactone+Al-H Alkyl-OH → Aldehyde Diels-Alder, Quinone Enone epoxidation, nucleophilic Wittig-methyl Enone epoxidation, nucleophilic Sulfoxide-Ei → Enone Ketone → Enone Pd/Sn-Vinyl+Vinyl-X Stille coupling Radical reduction(C-I) Ketone → EnolTriflate Ketone → Ketone-α-OR Ketone enolate+(Ox) Diels-Alder, Intram |
Reagents: | Dioxirane BH4-Na+ Periodate, sodium Acetic anhydride Fluoride, R4N+ BH4-Na+ Cr2O7·2PyH (PDC) H2O2, NaOH Vinyl-Sulfide PdCl2(PPh3)2 Fluoride, R4N+ Sulfonyl chloride, methane Epoxide LiSnR3 Carbodiimide DMAP PPh3=CH2 AlHiBu2 Cr2O7·2PyH (PDC) Photochemistry I2 Iodosobenzene-OAc HSnPh3 AIBN AlMe3 Dess-Martin H2O2, NaOH O2, tBuOK P(OEt)3 Dioxirane Quinone |