Total synthesis of Myrocin C:
| Reference: | Chu-Moyer, M. Y.; Danishefsky, S. J.; Schulte, G. K. J. Am. Chem. Soc. 1994, 116, 11213. DOI |
| Reactions: | Enone → Allyl-OH • Mechanism • Bicyclo(410) • CompE+-Aldehyde/CarboxEster+Wittig • Diels-Alder, Quinone • Bicyclo(222) • Bicyclo(440) • Enone epoxidation, nucleophilic • Wittig-methyl • Enone epoxidation, nucleophilic • Alkene isomerization • CompOx-Enone/Alkene+ROOH • Sulfoxide-Ei → Enone • Ketone → Enone • Pd/Sn-Vinyl+Vinyl-X • Radical reduction(C-I) • Alkyl-X → Alkyl-H(2°) • Ketone → EnolTriflate • Ketone → Ketone-α-OR • Diels-Alder, Intram, Ene • Lactone-5 • Bicyclo(440) • Ketone → Ketone-α-OR • Diol-1,2 cleavage • Lactone-5 • O-H → O-C(O)R • Allyl-OH → Enone • O-SiMe2tBu → O-H • O-H → O-SO2Me • Lactone → Lactol • CompRed-Lactone/Lactone+M-H • C-CO2H → C-I • Epoxide+M-SR • Thiolate+Epoxide • Aldehyde → Alkyl-OH • CompRed-Aldehyde/CarboxEster+M-H • O-H → O-SiMe2tBu • O-H → O-C(O)R • Alkyl-OH → Aldehyde • Sulfide → Sulfoxide • O-SiMe2tBu → O-H • O-C(O)R → O-H • |
| Reagents: | Butadiene, 2-OR • BH4-Na+ • Periodate, sodium • Acetic anhydride • Fluoride, R4N+ • BH4-Na+ • SiMe2tBu-Cl • Cr2O7·2PyH (PDC) • H2O2, NaOH • EneSulfide • PdCl2(PPh3)2 • Fluoride, R4N+ • Sulfonyl chloride, methane • Epoxide • SnR3-Li • Carbodiimide • DMAP • PPh3=CH2 • AlHiBu2 • Cr2O7·2PyH (PDC) • Photochemistry • I2 • Iodosobenzene-OAc • HSnPh3 • AIBN • AlMe3 • Dess-Martin • H2O2, NaOH • KOtBu • P(OEt)3 • Dioxirane • Quinone • Dioxirane • NaOMe • AlMe3 • |