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Total synthesis of Zygosporin E:
Reference: Vedejs, E.; Reid, J. G.; Rodgers, J. D.; Wittenberger, S. J. J. Am. Chem. Soc. 1990, 112, 4351-4357. DOI. Vedejs, E.; Wittenberger, S. J. J. Am. Chem. Soc. 1990, 112, 4357-4364. DOI
Keywords: Selenide → Selenoxide • Photochemistry • O-SiMe2tBu → O-H • Sulfide → Sulfonium • N-C(O)R → N-H • N-H → N-SiMe2tBu • N-SiR3 → N-H • O-H → O-C(O)R • Sulfide → Sulfonium • Selenide → Selenoxide • Selenoxide 2,3-Sigmatropic • Si-Allyl → RSe-Allyl • Sulfide → Sulfoxide • Sulfoxide-Ei → Ene • Ketone-α-S(O)nR → Ketone • Ketone enolate+Me-I • Claisen acylation, acyl-X • CarboxAmide enolate+Acyl-X • CarboxCl+Enolate • Selenoxide-Ei → EneLactam • Diels-Alder, Enone • Allyl-OH → Allyl-Cl • Mitsunobu → Cl • Ketone enolate+Me-I • 2,3-Sigmatropic Ylide-N/O/S • Ketone epimerization • N-C(O)R → N-H • Ketone → Alkyl-OH • N-H → N-C(O)R • Diels-Alder, Thioaldehyde • Sulfide-6 • CompOx-Selenide/Sulfide+Iodate •
Reagents: Mesityl-Li • Chloroacetate • NaH • SePh-Cl • Perbenzoic acid, 3-chloro • Thiol, phenacyl • Photochemistry • HF·NEt3 • PBu3, CCl4 • LiNiPr2 • MeI • Carbonate, potassium • SiMe2tBu-Cl • LiN(SiMe3)2 • MeI • HF·NEt3 • Acetic anhydride • Me3O+ X- • Zn° • SePh-SeR2+ • Periodate, sodium • Perbenzoic acid, 3-chloro • Diselenide, phenyl • Me3O+ X- • Butadiene, 2-OR • AlHiBu2 • Acetic anhydride, DMAP •

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