Total synthesis of Norleucosceptroid A:
| Reference: | Hugelshofer. C. L.; Magauer, T. Angew. Chem. Int. Ed. 2014, 53, 11351-11355. DOI |
| Reactions: | Alkyl-OH → Aldehyde • Wittig-ketenylidine • Lactone-5 • Wittig (intram) • Ketone → EnolTriflate • EnoateEster → Allyl-OH • Pd-Carboxylation • EnolTriflate → EnoateEster • ConjAdd-Acylation (intram) • Diels-Alder, EnoateEster • Bicyclo(430) • Hydrogenation Enone • Retro-Claisen • Lactone → Lactol • Aldol-Acid → Aldol • Bicyclo(221)-oxa • Bicyclo(430) • Mechanism • Lactol → Lactone • Dehydroalkoxylation → EnoateEster • Cu-Me+EnoateEster • EnoateEster+Cu-R • ConjAdd Cu-Me • CarboxEster → Enol • EnolEther → Epoxide • EnolEther → Aldehyde-α-OR • Al-Vinyl+Epoxide • Alkyl-OH → Ketone • O-PMB → O-H • Ketone → Ketone-α-OR • Alkyl-OH → Aldehyde • Aldehyde → Acetal • HWE → DienoateEster • |
| Reagents: | DMSO, Py·SO3 (Parikh-Doering) • PPh3=C=C=O • LiNiPr2 • Tf2O • AlHiBu2 • Pd(PPh3)4, CO • Chloride, lithium • LiN(SiMe3)2 • H2, Pd • NEt3 • Acetic acid, trifluoro • AlHiBu2 • Cr2O7·2PyH (PDC) • LiNiPr2 • Me-Cuprate • AlHiBu2 • Sulfonyl chloride, methane, NEt3 • Dioxirane • Cr2O7·2PyH (PDC) • Ceric ammonium nitrate • LiN(SiMe3)2 • O2 • IBX • P(O)(OR)2CH2-Vinyl • KOtBu • |