Synthesis of thienodolin
2004 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 12, 2589-2592 p.Article in journal (Refereed) Published
We report a total synthesis of the alkaloid thienodolin (1a), as well as its 5-chloro isomer 1b and its unsubstituted analogue 1c, in three steps from the corresponding oxindoles Ba-c. The preparation was achieved through an initial Vilsmeier-Haack-Arnold reaction (chloro-formylation) followed by protection at the indole nitrogen, creation of the fused thiophene ring by nucleophilic substitution at the 2-position and an intramolecular cyclization using mercaptoacetamide. This gave 1a, 1b and 1c in total yields of 42%, 35% and 37%, respectively.
Place, publisher, year, edition, pages
2004. no 12, 2589-2592 p.
IdentifiersURN: urn:nbn:se:sh:diva-15474DOI: 10.1002/ejoc.200400073ISI: 000222295800007ScopusID: 2-s2.0-4544251222OAI: oai:DiVA.org:sh-15474DiVA: diva2:504676