Total synthesis of Hirsutene (Hudlicky):
| Reference: | Hudlicky, T.; Kutchan, T. M.; Wilson, S. R.; Mao, D. T. J. Am. Chem. Soc. 1980, 102, 6351. DOI |
| Reactions: | Claisen-Johnson • 1,3-Sigmatropic • Cyclopentene • Bicyclo(330) • Wittig-methyl • Mg-Vinyl+Aldehyde • Enal+Mg-R • Cyclopropanation Diazoketone • Cyclopentanone • Bicyclo(310) • Diazoketone • CarboxCl → Diazoketone • Alkene isomerization • CompRed-Alkene/Ketone+H2 • Hydrogenation Alkene • CarboxAcid → CarboxCl • CarboxEster → CarboxAcid • |
| Reagents: | Orthoacetate • Hg(OAc)2 • Oxalyl chloride • Diazoethane • Diazoketone • Cu(acac)2 • RhCl3 • H2, Pt • PPh3=CH2 • Hydroxide, potassium • Vinyl-MgX • |