Facile two-step chemoenzymatic access to natural germination inhibitor (+)-erigeronic acid A
| Title | Facile two-step chemoenzymatic access to natural germination inhibitor (+)-erigeronic acid A |
| Publication Type | Journal Article |
| Year of Publication | 2006 |
| Authors | Gogoi, S, Argade, NP |
| Journal | Tetrahedron |
| Volume | 62 |
| Issue | 13 |
| Pagination | 2999-3003 |
| Date Published | MAR |
| Type of Article | Article |
| ISSN | 0040-4020 |
| Keywords | (+)-erigeronic acid, (R)acetoxysuccinic anhydride, natural germination inhibitor, primary enolate of butyl methyl ketone, synthesis |
| Abstract | A facile two-step synthesis of natural germination inhibitor 5-butyl-3-oxo-2,3-dihydrofuran-2-yl-acetic acid [(+)-erigeronic acid A, 1] has been described via highly regioselective ring opening of (R)-acetoxysuccinic anhydride with the primary enolate of butyl methyl ketone, followed by an enzymatic hydrolysis and ail in situ dehydrative cyclization pathway with 77% overall yield. Oil the basis of the present chemoenzymatic approach, (R)-configuration has been assigned to the C-2 chiral centre of the natural erigeronic acid. (c) 2006 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tet.2006.01.044 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.645 |
Divison category:
Organic Chemistry