Lactam analogues of galiellalactone

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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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Research areas and keywords

Subject classification (UKÄ) – MANDATORY

  • Organic Chemistry

Keywords

  • Galiellalactone, Aza-keto galiellalactams, STAT3 inhibitor, Amide, coupling/intramolecular Michael, addition
Original languageEnglish
Pages (from-to)3336-3341
JournalTetrahedron
Volume68
Issue number16
Publication statusPublished - 2012
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

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)