Total synthesis of Hirsutene (Curran):
| Reference: | Curran, D. P.; Rakiewicz, D. M. J. Am. Chem. Soc., 1985, 107, 1448. DOI |
| Reactions: | O-THP → O-H • CarboxAcid → Alkyl-OH • O-H → O-Tf • Alkyl-X → Alkyl-I • Finkelstein reaction • Claisen-Ireland • Selenolactonization • Lactone-5 • Li-Alkynyl+Alkyl-X • Li/H → Li-Alkynyl • Alkyl-X+Li-R • CompE+-Alkyl-X/Alkyl-X+M-R • Cu-Alkyl+Alkyl-X • Cu-Allyl+Alkyl-X • Selenoxide-Ei → Allyl-OR • Alkyl-OH → Alkyl-I • Radical cyclization(Alkyl) • Cyclopentane • Bicyclo(330) • Si-Alkynyl → H-Alkynyl • Luche reduction • Enone → Allyl-OH • |
| Reagents: | BH4-Na+, CeCl3 • LiNiPr2 • SePh-Cl • H2O2 • Alkyl-Li • CuBr • AlHiBu2 • Tf2O • Iodide, R4N+ • Fluoride, cesium • Alkynyl-Li • Li°/Naphth • HSnBu3 • AIBN • |