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Synthesis of thienodolin
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science.
Södertörn University, School of Chemistry, Biology, Geography and Environmental Science. Karolinska Institutet.
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
Abstract [en]

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.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:sh:diva-15474DOI: 10.1002/ejoc.200400073ISI: 000222295800007ScopusID: 2-s2.0-4544251222OAI: oai:DiVA.org:sh-15474DiVA: diva2:504676
Available from: 2012-02-21 Created: 2012-02-20 Last updated: 2014-04-16Bibliographically approved

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Bergman, Jan
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