Lactam analogues of galiellalactone
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/2571006
- author
- Nilsson, Jakob LU ; Gidlöf, Ritha LU ; Johansson, Martin H LU and Sterner, Olov LU
- organization
- publishing date
- 2012
- 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
- additional info
- 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)
- id
- b8bc7a5b-efaa-4ba7-8e48-a2fc934b0458 (old id 2571006)
- date added to LUP
- 2016-04-01 15:00:42
- date last changed
- 2022-01-28 03:37:36
@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}}, keywords = {{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}}, doi = {{10.1016/j.tet.2012.02.065}}, volume = {{68}}, year = {{2012}}, }