Total synthesis of Hirsutene (Funk):
| Reference: | Funk, R. L.; Bolton, G. L. J. Org. Chem. 1984, 49, 5021. DOI |
| Reactions: | Sakurai allylation • Si-Allyl+Enone • Enone+Si-R • ConjAdd Si-Allyl • Ketone → Nitrone • Nitrone synthesis • Nitrone Cycloaddition • Cyclopentane • Bicyclo(330) • N-OR → N-H • Alkyl-OH → Ketone • Hydrogenation alkene • Cope elimination • Amine → AmineOxide • |
| Reagents: | Allyl-SiR3 • TiCl4 • NHMe(OH) • NaOEt • MeI • H2, Pd • Bicarbonate, sodium • CrO3Cl·PyH (PCC) • H2, Pd • Perbenzoic acid, 3-chloro • |