| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5276525 | Tetrahedron Letters | 2007 | 4 Pages |
Abstract
A simple and efficient synthetic route to the bicyclic α,β-unsaturated β-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-5-carboxylate, a versatile intermediate in the synthesis of biologically active unsaturated 1,4-dialdehydes, is described. The synthesis includes a chirality introducing nonenzymatic asymmetric desymmetrization (ADS) reaction of a cyclic meso-anhydride 4 and a modified Hofmann method for preparing exocyclic dienes. The ester was synthesized in a moderate overall yield (19%) from 6 and with an excellent enantioselectivity (>90%).
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Daniel Röme, Martin Johansson, Olov Sterner,