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Total synthesis of Guanacastepene A:
Reference: Boyer, F. D.; Hanna, I.; Ricard, L. Org. Lett. 2004, 6, 1817. DOI
Keywords: Pd/Sn-Vinyl+Vinyl-X • Stille coupling • ConjAdd Enolate • Ketone enolate+EneNitrile • Reductive cyanation • Li-Isocyanide • Li/H → Li-Alkynyl • O-H → O-SiMe2tBu • EnoateEster → Allyl-OH • O-SiMe2tBu → O-H • Diol-1,3 → Ketal • Allyl-OH → Enone • Seyferth-Gilbert homologation • Aldehyde → Alkyne • Li-Nitrile+Alkyl-X • Alkyl-X+Enolate • Li-Alkynyl+Chlorocarbonate • Enyne metathesis • Nitrile+Mg-R → Ketone • Mg-Alkyl+Nitrile • Nitrile → Aldehyde • Epoxide → Allyl-OH • Ketone → EnolTriflate • Epoxidation, peracid • Mechanism •
Reagents: Acrylonitrile • NaOMe • Pyridine, 2,6-di-tBu • Pd(PPh3)4 • MeMgBr • TsCH2NC • LiN(SiMe3)2 • AlHiBu2 • Diazophosphonate • Carbonate, potassium • BuLi(n) • Perbenzoic acid, 3-chloro • Yb(OTf)3 • SiMe2tBu-OTf • AlHiBu2 • Fluoride, R4N+ • Me2C(OMe)2 • Dess-Martin • Grubbs II • NiCl2 • O=C(OR)Cl • KOtBu • DMSO (solvent) •

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