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A facile two-step chemoenzymatic access to natural germination inhibitor (+)-erigeronic acid A
- Source :
- Tetrahedron. 62:2999-3003
- Publication Year :
- 2006
- Publisher :
- Elsevier BV, 2006.
-
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 an in situ dehydrative cyclization pathway with 77% overall yield. On the basis of the present chemoenzymatic approach, (R)-configuration has been assigned to the C-2 chiral centre of the natural erigeronic acid.
Details
- ISSN :
- 00404020
- Volume :
- 62
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........512b2e908c3c2581e25f97512bec5dab