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An efficient synthesis of pregaliellalactone and desoxygaliellalactone

Furuseth, Eira Ruud LU ; Larsson, Rikard LU ; Blanco, Narda LU ; Johansson, Martin H LU and Sterner, Olov LU (2014) In Tetrahedron Letters 55(27). p.3667-3669
Abstract
A short and efficient total synthesis of rac-desoxygaliellalactone and (+)-desoxygaliellalactone, via the biosynthetic intermediate pregaliellalactone, is described. The synthesis was achieved in only three steps, for (+)-desoxygaliellalactone including an enantioselective alkyl propiolate addition to 4-pentenal, a palladium catalysed alkylative lactonisation and an intramolecular Diels-Alder cycloaddition. (C) 2014 Elsevier Ltd. All rights reserved.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Natural product, Pregaliellalactone, Desoxygaliellalactone, Galiellalactone, Enantioselective, Biosynthesis
in
Tetrahedron Letters
volume
55
issue
27
pages
3667 - 3669
publisher
Elsevier
external identifiers
  • wos:000337996900007
  • scopus:84902158573
ISSN
0040-4039
DOI
10.1016/j.tetlet.2014.04.117
language
English
LU publication?
yes
id
2355bb4c-c247-4cf4-acba-980a59ec72b3 (old id 4608880)
date added to LUP
2014-08-29 10:33:58
date last changed
2017-07-23 04:21:37
@article{2355bb4c-c247-4cf4-acba-980a59ec72b3,
  abstract     = {A short and efficient total synthesis of rac-desoxygaliellalactone and (+)-desoxygaliellalactone, via the biosynthetic intermediate pregaliellalactone, is described. The synthesis was achieved in only three steps, for (+)-desoxygaliellalactone including an enantioselective alkyl propiolate addition to 4-pentenal, a palladium catalysed alkylative lactonisation and an intramolecular Diels-Alder cycloaddition. (C) 2014 Elsevier Ltd. All rights reserved.},
  author       = {Furuseth, Eira Ruud and Larsson, Rikard and Blanco, Narda and Johansson, Martin H and Sterner, Olov},
  issn         = {0040-4039},
  keyword      = {Natural product,Pregaliellalactone,Desoxygaliellalactone,Galiellalactone,Enantioselective,Biosynthesis},
  language     = {eng},
  number       = {27},
  pages        = {3667--3669},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {An efficient synthesis of pregaliellalactone and desoxygaliellalactone},
  url          = {http://dx.doi.org/10.1016/j.tetlet.2014.04.117},
  volume       = {55},
  year         = {2014},
}