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Enantioselective formal synthesis of tridemethylisovelleral

Röme, Daniel LU ; Johansson, Martin H LU and Sterner, Olov LU (2007) In Tetrahedron Letters 48(4). p.635-638
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%).
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
48
issue
4
pages
635 - 638
publisher
Elsevier
external identifiers
  • wos:000243704000026
  • scopus:33845599129
ISSN
0040-4039
DOI
10.1016/j.tetlet.2006.11.122
language
English
LU publication?
yes
id
38e3dcdd-9fba-4ce6-9197-d0f5ae19d2cb (old id 675389)
date added to LUP
2007-12-20 14:54:59
date last changed
2017-01-01 06:49:10
@article{38e3dcdd-9fba-4ce6-9197-d0f5ae19d2cb,
  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%).},
  author       = {Röme, Daniel and Johansson, Martin H and Sterner, Olov},
  issn         = {0040-4039},
  language     = {eng},
  number       = {4},
  pages        = {635--638},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {Enantioselective formal synthesis of tridemethylisovelleral},
  url          = {http://dx.doi.org/10.1016/j.tetlet.2006.11.122},
  volume       = {48},
  year         = {2007},
}