Total synthesis of Hirsutene (Cohen):
| Reference: | Ramig, K.; Kuzemko, M. A.; McNamara, K.; Cohen, T. J. Org. Chem. 1992, 57, 1968. DOI |
| Reactions: | Wittig-methyl • Ketal(thio) → CH2 • Alkyl-OH → Alkyl-H(2°) • Li-Sulfide+Ketone • ConjAdd Li-R • Ketone enolate oxidation • Oxidative coupling enolate • Cyclopentanone • Bicyclo(330) • Li/S → Li-Alkyl • Enone+Li-R • CompE+-Ketone/Ketone+glycol • Ketone → Ketal • Ketone → Alkyl-OH • O-H → O-P(O)X2 • Ketal → Ketone • |
| Reagents: | RaNi • TsOH • Li°/NH3 • BuLi(n) • P(O)NMe2Cl2 • NHMe2 • Li°/MeNH2 • TsOH • PPh3=CH2 • Glycol • LiC(SR)3 • BuLi(sec) • FeCl3 • DMF (solvent) • |