A new approach to rethrolone synthesis
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 2,p. 467-469
- https://doi.org/10.1039/p19830000467
Abstract
Rearrangement of the 4-ylidenebutenolides (4) and (5), with sodium methoxide in methanol, leads to the cyclopent-2-ene-1,4-diones (6), which when heated with sodium chloride in dimethyl sulphoxide give the 1,4-diones (7). The latter can be reduced using zinc in acetic acid, to the dihydrorethrolones (8). In a similar manner, rearrangement of (10) produces (11a) which can be demethoxycarbonylated to (11b), an intermediate used previously in a synthesis of natural jasmololone (8; R = EtCH:CH).This publication has 1 reference indexed in Scilit:
- Synthetic approaches towards 4-ylidenebutenolides and 4-ylidenetetronic acids. Regioselective nucleophilic additions to unsymmetrically substituted maleic anhydridesJournal of the Chemical Society, Perkin Transactions 1, 1979