Total synthesis of Seychellene (Piers):
| Reference: | Piers, E.; de Waal, W.; Britton, R. W. J. Am. Chem. Soc. 1971, 93, 5113–5120. DOI |
| Reactions: | O-THP → O-H • ConjAdd-Acylation • Ketone enolate+CarboxCl • Cu-Me+Enone • Epoxidation, peracid • Epoxide rearrangement • Wittig-methyl • CompE+-Ketone/CarboxEster+Wittig • Hydrogenation Alkene • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Ketone → C=CH2 • Hydroboration → Alkyl-OH • O-H → O-SO2Ar • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Cyclohexanone • Bicyclo(222) • Ketone → Alkyl-OH • CompRed-Ketone/Enone+M-H • O-C(O)R → O-H • Alkyl-OH → Ketone • Alkyl-OH → Ketone • Ketone+Li-Alkyl • Li-Me+Ketone • Dehydration → Ene • Ketone → C=CH2 • O-H → O-THP • |
| Reagents: | Wieland-Miescher • BH4-Na+ • Me-Cuprate • Acetyl chloride • PPh3=CH2 • PPh3 • Hydroxide, potassium • CrO3·Py2 (Collins) • Me-Li • SOCl2 • BH3·THF • H2O2, NaOH • TsCl, Py • TsOH • CrO3·Py2 (Collins) • NaH • Me-Li • DMSO (solvent) • SOCl2 • DHP • Perbenzoic acid, 3-chloro • |