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Lactam analogues of galiellalactone

Nilsson, Jakob LU ; Gidlöf, Ritha LU ; Johansson, Martin H LU and Sterner, Olov LU (2012) In Tetrahedron 68(16). p.3336-3341
Abstract
A synthetic route to lactam analogues of the fungal STAT3 inhibitor galiellalactone is presented. The synthesis involves a one-pot tosylamide amide coupling/intramolecular Michael addition and an introduction of an alpha,beta-unsaturation, regioselectively directed by the tosyl functionality. An iodolactonization of the octahydroindolizine 9 and a re-opening of the lactone were employed for introducing an iodo substituent, facilitating the preparation of 8-substituted analogues (e.g., 4) using a Suzuki cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Galiellalactone, Aza-keto galiellalactams, STAT3 inhibitor, Amide, coupling/intramolecular Michael, addition
in
Tetrahedron
volume
68
issue
16
pages
3336 - 3341
publisher
Elsevier
external identifiers
  • wos:000303035600008
  • scopus:84859155568
ISSN
0040-4020
DOI
10.1016/j.tet.2012.02.065
language
English
LU publication?
yes
id
b8bc7a5b-efaa-4ba7-8e48-a2fc934b0458 (old id 2571006)
date added to LUP
2012-06-04 09:53:34
date last changed
2017-01-01 06:33:15
@article{b8bc7a5b-efaa-4ba7-8e48-a2fc934b0458,
  abstract     = {A synthetic route to lactam analogues of the fungal STAT3 inhibitor galiellalactone is presented. The synthesis involves a one-pot tosylamide amide coupling/intramolecular Michael addition and an introduction of an alpha,beta-unsaturation, regioselectively directed by the tosyl functionality. An iodolactonization of the octahydroindolizine 9 and a re-opening of the lactone were employed for introducing an iodo substituent, facilitating the preparation of 8-substituted analogues (e.g., 4) using a Suzuki cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.},
  author       = {Nilsson, Jakob and Gidlöf, Ritha and Johansson, Martin H and Sterner, Olov},
  issn         = {0040-4020},
  keyword      = {Galiellalactone,Aza-keto galiellalactams,STAT3 inhibitor,Amide,coupling/intramolecular Michael,addition},
  language     = {eng},
  number       = {16},
  pages        = {3336--3341},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Lactam analogues of galiellalactone},
  url          = {http://dx.doi.org/10.1016/j.tet.2012.02.065},
  volume       = {68},
  year         = {2012},
}