Total Syntheses

Reaction scheme for total synthesis of the natural product Phorocantholide J (Petrzilka)
Total synthesis of Phorocantholide J (Petrzilka):
Reference:Petrzilka, M. Helv. Chim. Acta 1978, 61, 3075. DOI
Reactions:Selenoxide-Ei → Enol ether • Selenoetherification • Ether-8 • Claisen-Ketene acetal • Lactone-9+ • Li-Alkyl+Aldehyde • Enal+Li-R • Ketone → Alkyl-OH • O-H → O-Vinyl • Selenide → Selenoxide • Li/Cl → Li-Alkyl •
Reagents:BH4-Na+ • Vinyl-OR • Alkyl-Li • Li°/Naphth • SePh-Br • NEtiPr2 • Periodate, sodium • Sulfate, magnesium • Hg(OAc)2 • Acrolein •