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Total synthesis of Myrocin C:
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 •

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