Concepedia

Synthesis of the Complete Carbocyclic Skeleton of Vinigrol

L. Gentric, Issam Hanna, Louis Ricard

Organic Letters · 2003 · 44 citations · 13 references

DOI

Concepts

Abstract

[reaction: see text] An efficient entry to the fully elaborated skeleton of vinigrol is described. The installation of the desired stereochemistry at C(12) and the construction of the eight-membered ring were achieved in one operation by a remarkably facile anionic oxy-Cope rearrangement of Z-isopropenyl isomer 24.

References

13

Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects

André Luís Gemal, Jean Louis Luche · Journal of the American Chemical Society · 1981 · 1K citations

, , +5

Synthesis of halo enol lactones. Mechanism-based inactivators of serine proteases

Grant A. Krafft, John A. Katzenellenbogen · Journal of the American Chemical Society · 1981 · 194 citations

, , +8

Oxidative cleavage of silicon-carbon bonds in organosilicon fluorides to alcohols

Kohei Tamao, Toshio Kakui, Munetaka Akita et al. · Tetrahedron · 1983 · 193 citations

, , +10

Control of ring junction stereochemistry via radical cyclization

Gilbert Stork, Michaël Kahn · Journal of the American Chemical Society · 1985 · 185 citations

, , +7

Reduction by a model of NAD(P)H. Effect of metal ion and stereochemistry on the reduction of .alpha.-keto esters by 1,4-dihydronicotinamide derivatives

Yutaka Ohnishi, Masayuki Kagami, Atsuyoshi Ohno · Journal of the American Chemical Society · 1975 · 164 citations

, , +8