An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives

Pilho Kim, Jennifer M. Tsuruda, Marilyn M. Olmstead, Shawn Eisenberg, Mark J. Kurth

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

A one-pot route to 3-benzo[b]thiophen-2-yl-acrylates (2) from the corresponding thiophenols (1) is reported. Ester reduction and subsequent hydroxyl esterification deliver psuedo trienoates (II) which undergo an intramolecular Diels-Alder (IMDA) reaction to give two 2-oxa-9-thiacyclopenta[b]fluoren-3-one products (I) - the major Diels-Alder product rearomatizes to 7.

Original languageEnglish (US)
Pages (from-to)3963-3966
Number of pages4
JournalTetrahedron Letters
Volume43
Issue number21
DOIs
StatePublished - May 20 2002

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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    Kim, P., Tsuruda, J. M., Olmstead, M. M., Eisenberg, S., & Kurth, M. J. (2002). An intramolecular Diels-Alder route to novel tetracyclic benzo[b]thiophene derivatives. Tetrahedron Letters, 43(21), 3963-3966. https://doi.org/10.1016/S0040-4039(02)00565-8