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Lactam analogues of galiellalactone

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Author

Summary, in 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.

Publishing year

2012

Language

English

Pages

3336-3341

Publication/Series

Tetrahedron

Volume

68

Issue

16

Document type

Journal article

Publisher

Elsevier

Topic

  • Organic Chemistry

Keywords

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

Status

Published

ISBN/ISSN/Other

  • ISSN: 0040-4020