Enantioselective formal synthesis of tridemethylisovelleral
Research output: Contribution to journal › Article
Abstract
A simple and efficient synthetic route to the bicyclic alpha,beta-unsaturated beta-keto ester methyl (3aS,7aS)-6-oxo-2,3,3a,6,7,7ahexahydro-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 nieso-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%).
Details
| Authors | |
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| Organisations | |
| Research areas and keywords | Subject classification (UKÄ) – MANDATORY
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| Original language | English |
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| Pages (from-to) | 635-638 |
| Journal | Tetrahedron Letters |
| Volume | 48 |
| Issue number | 4 |
| Publication status | Published - 2007 |
| Publication category | Research |
| Peer-reviewed | Yes |
Bibliographic note
The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
