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An intramolecular Diels-Alder route to racemic quadrone

✍ Scribed by Schlessinger, R. H.; Wood, J. L.; Poss, A. J.; Nugent, R. A.; Parsons, W. H.


Book ID
127125079
Publisher
American Chemical Society
Year
1983
Tongue
English
Weight
278 KB
Volume
48
Category
Article
ISSN
0022-3263

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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-