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 |
| Reactions: | Selenide → Selenoxide • Photochemistry • Sulfide → Sulfonium • N-C(O)R → N-H • N-H → N-SiMe2tBu • Sulfide → Sulfonium • Selenide → Selenoxide • Selenoxide 2,3-Sigmatropic • Si-Allyl → Se-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 • Appel → Cl • Ketone enolate+Me-I • 2,3-Sigmatropic Ylide-N/O/S • Ketone epimerization • N-H → N-C(O)R • Diels-Alder, Thioaldehyde • Sulfide-6 • CompOx-Selenide/Sulfide+Iodate • Alkyl-X → Alkyl-SR • Thioaldehyde • Lactam → Lactam-α-SeR • N-C(O)R → N-H • Ketone → Alkyl-OH • N-H → N-C(O)R • O-H → O-C(O)R • Allyl-X → Allyl-Sulfonium • N-SiR3 → N-H • N-H → N-C(O)R • Sulfide → Sulfonium • O-SiMe2tBu → O-H • |
| 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, DMAP • Me3O+ X- • Zn° • SePh-SeR2+ • Periodate, sodium • Perbenzoic acid, 3-chloro • Diselenide, phenyl • Me3O+ X- • Butadiene, 2-OR • AlHiBu2 • Acetic anhydride, DMAP • |