Concepedia

An Approach to the Synthesis of the Eupomatilones

Sang‐Phyo Hong, Matthias C. McIntosh

Organic Letters · 2001 · 34 citations · 3 references

DOI

Concepts

Abstract

[structure: see text] A concise approach to the eupomatilone family of lignans is presented. The strategy employs an intramolecularly competitive Ireland-Claisen rearrangement of a densely functionalized bis-allylic ester. The rearrangement serves both to construct the A-ring and to establish the stereochemistry at C(3) and C(4).

References

3

Existence of stable structural isomers of ketene. A theoretical study of the C2H2O potential energy surface

Willem J. Bouma, Ross H. Nobes, Leo Radom et al. · The Journal of Organic Chemistry · 1982 · 85 citations

, , +16

Photoinduced Molecular Transformations. 157. A New Stereo- and Regioselective Synthesis of 2,6-Diaryl-3,7-dioxabicyclo[3.3.0]octane Lignans Involving a .beta.-Scission of Alkoxyl Radicals as the Key Step. New Total Syntheses of (.+-.)-Sesamin, (.+-.)-Eudesmin, and (.+-.)-Yangambin

Hiroshi Suginome, Masataka Ishikawa, Kaoru Yorita et al. · The Journal of Organic Chemistry · 1995 · 64 citations

, , +10

Ozonolysis of trans-2,3-dichloro-2-butene. Isolation of .alpha.-chloro peroxides

Karl Griesbaum, Peter Hofmann · Journal of the American Chemical Society · 1976 · 44 citations

, , +6