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Lactam analogues of galiellalactone

Author:
  • Jakob Nilsson
  • Ritha Gidlöf
  • Martin H Johansson
  • Olov Sterner
Publishing year: 2012
Language: English
Pages: 3336-3341
Publication/Series: Tetrahedron
Volume: 68
Issue: 16
Document type: Journal article
Publisher: Elsevier

Abstract english

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.

Keywords

  • Organic Chemistry
  • Galiellalactone
  • Aza-keto galiellalactams
  • STAT3 inhibitor
  • Amide
  • coupling/intramolecular Michael
  • addition

Other

Published
  • ISSN: 0040-4020
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

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Faculty of Science

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