Total synthesis of Aromadendrene:
| Reference: | Büchi, G.; Hofheinz, W. Paukstelis, J. V. J. Am. Chem. Soc. 1966, 88, 4113–4114. DOI J. Am. Chem. Soc. 1969, 91, 6473. |
| Reactions: | Aldehyde → Alkyl-OH • Alkyl-SO2R → Alkyl-H • Alkene → Alkyl-Br • Enal enolate+Alkyl-X (3°) • Cyclopropane • Alkyl-X+Enolate (intram) • Bicyclo(410) • Wittig-methyl → Diene • Wittig-methyl • Diels-Alder, Enal • Bicyclo(440) • Alkene → Diol-1,2 • Semipinacol • Mechanism • Cycloheptane • Cyclopentane • Bicyclo(530) • O-H → O-SO2Ar • CompNu-O-H/O-H+RSO2X • Aldehyde → CH3 • O-H → O-SO2Me • |
| Reagents: | HBr • Acetic acid • KOtBu • PPh3=CH2 • Acrolein • KOtAm • AlH4-Li+ • Sulfonyl chloride, methane • AlH4-Li+ • OsO4 • TsCl, Py • KOtBu • PPh3=CH2 • |