An Ireland-Claisen approach to lignans: Synthesis of the putative structure of 5-epi-eupomatilone-6
by Hutchison, John Michael; Hong, Sang Phyo; McIntosh, Matt 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 of Organic Chemistry
- Start Page
- 0022-3263; 1520-6904