An Ireland-Claisen approach to lignans: synthesis of the putative structure of 5-epi-eupomatilone-6 |
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| Authors: | Hutchison John M Hong Sang-Phyo McIntosh Matthias C |
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| Institution: | Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, Arkansas 72701, USA. |
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| Abstract: | 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. |
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