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

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