An Ireland-Claisen approach to lignans: Synthesis of the putative structure of 5-epi-eupomatilone-6
by Hutchison, John M.; Hong, Sang-Phyo; McIntosh, Matthias C.
A novel Ireland-Claisen approach to the putative structure of eupomatilone-6 is described. The rearrangement established the C3 and C4 stereocenters and concomitantly generated a vinyl epoxide. The C5 oxygen was installed by cyclization of the pentenoic acid carboxyl group onto the vinyl epoxide in an S(N)2' fashion to afford the C5-epi stereochemistry. The natural C5 stereochemistry was accessed via a substrate directed dihydroxylation.
- Journal
- Journal of Organic Chemistry
- Volume
- 69
- Issue
- 12
- Year
- 2004
- Start Page
- 4185-4191
- URL
- https://dx.doi.org/10.1021/jo049817r
- ISBN/ISSN
- 1520-6904; 0022-3263
- DOI
- 10.1021/jo049817r