image

Total synthesis of Deacetoxyalcyonin Acetate:
Reference: MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 1995, 117, 10391. DOI
Keywords: Enone → EnolTriflate • O-H → O-Methoxypropyl • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde-α-OR • O-H → O-Piv • O-H → O-SiMe2tBu • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • O-H → O-C(O)R • O-SiMe2tBu → O-H • Si-Alkynyl → H-Alkynyl • Li-Alkynyl+Epoxide • Epoxide+Li-R • Li/H → Li-Alkynyl • Wittig-methoxymethyl • Reductive formylation • Li/I → Li-Vinyl • Nozaki-Hiyama coupling • Cr-Vinyl+Aldehyde • Aldehyde+Cr-R • Sharpless epoxidation • Decarbonylation • Sn-Vinyl → I-Vinyl • Pd-Stannylation • Epoxide reduction • Haloboration Alkyne • Alkyne → Vinyl-I • Photochemistry • Decarbonylation • Felkin-Anh • Li-Aryl+Aldehyde • Prins-Pinacol • Ether-5 • Mechanism •
Reagents: B(I)-BBN • Acetic acid • LiNiPr2 • SnMe3-SnMe3 • NIS • BuLi(tert) • Epoxide • Alkynyl-Li • BF3·OEt2 • Propenyl-OR • AlHiBu2 • RuO4-Pr4N+, NMO • AlH2(OR)2-Na+ • Piv-Cl • SiMe2tBu-OTf • AlHiBu2 • RuO4-Pr4N+, NMO • PPh3=CH-OMe • TfOH • NiCl2 • CrCl2 • DMSO (solvent) • Acetic anhydride, Py • Fluoride, R4N+ • Tf2NPh • Photochemistry • Pd(PPh3)4 • BF3·OEt2

Syntheses Home