Lactam analogues of galiellalactone

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.

• Författare: Jakob Nilsson; Ritha Gidlöf; Martin H Johansson; Olov Sterner
• Avdelning/ar: Centrum för analys och syntes
• Publiceringsår: 2012
• Språk: Engelska
• Sidor: 3336-3341
• Publikation/Tidskrift/Serie: Tetrahedron
• Volym: 68
• Issue: 16
• Länkar: http://dx.doi.org/10.1016/j.tet.2012.02.065
• Dokumenttyp: Artikel i tidskrift
• Förlag: Elsevier
• Ämne: Organic Chemistry
• Nyckelord: Galiellalactone; Aza-keto galiellalactams; STAT3 inhibitor; Amide; coupling/intramolecular Michael; addition
• Status: Published
• ISBN/ISSN/Övrigt: ISSN: 0040-4020