Total synthesis of Sterekunthal:
| Reference: | Malerich, J. P.; Trauner, D. J. Am. Chem. Soc. 2003, 125, 9554. DOI |
| Reactions: | HWE → EnoateEster-cis • Aldol-enamine → Enone • Electrocyclic-6π • Ether-6 • Quinone synthesis • Retro-Diels-Alder → Diene • Diels-Alder, Intram, Ene • EnoateEster → Allyl-OH • O-H → O-THP • O-SiPh2tBu → O-H • Allyl-OH → Enal • O-THP → O-H • Allyl-OH → Enal • |
| Reagents: | P(O)(OCH2CF3)2CHR-C(O)OMe • KN(SiMe3)2 • AlHiBu2 • DHP • Fluoride, R4N+ • MnO2 • 18-crown-6 • Acetic acid • TsOH • DMSO, CF3CO2H (Moffat) • Butadiene, 1-OR • |