Total synthesis of Hirsutene (Yu):
| Reference: | Jiao, L.; Yuan, C.; Yu, Z.-X. J. Am. Chem. Soc. 2008, 130, 4421. DOI |
| Reactions: | Carbonylation • HWE → Enone • Simmons-Smith • Cyclopropane • Mukaiyama Aldol • Aldol-Si • Ketone+EnolSilane • Cyclopentanone • Bicyclo(330) • 2+5 Cycloaddition • Cyclooctane • Cyclopentane • Bicyclo(630) • Rh Carbonylative cycloaddition • Ketone → EnolSilane • Alkyl-OH → Alkyl-H(3°) • Radical reduction(C-OR) • Wittig-methyl • O-H → O-C(O)R • |
| Reagents: | KOtBu • SiMe2tBu-OTf • NEt3 • CH2I2, ZnEt2 • Rh(CO)2Cl • HCl, H2O • HSnBu3 • AIBN • PPh3=CH2 • O=C(CO2Me)Cl • DMAP • P(O)(OCH2CF3)2CHR-C(O)Me • |