Issue 0, 1981

Synthesis of linear 3-phenylpyranocoumarins: synthesis of robustin, robustic acid, and their methyl ethers

Abstract

The linear 3-phenylpyranocoumarins, viz., robustin (5b; R4= H), its methyl ether (5b; R4= Me), robustic acid (5c; R4= H), its methyl ether (5c; R4= Me), 4-methoxy-3-phenylxanthyletin (5a; R4= H), and its methyl ether (5a; R4= Me), have been synthesised starting from the corresponding 7-(1,1-dimethylprop-2-ynyloxy)-coumarin derivatives having the 8-position blocked with an easily introduceable and removable group like iodine. The subsequent step consists of heating the prop-2-ynyl ethers in NN-dimethylaniline, which resulted in cyclization to linear pyranocoumarins, accompanied by the removal of iodine and also partial demethylation of the methoxy-group at the 4-position. The compounds obtained were identical with the natural samples and were different from authentic samples of the corresponding angular isomers.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 1697-1702

Synthesis of linear 3-phenylpyranocoumarins: synthesis of robustin, robustic acid, and their methyl ethers

V. K. Ahluwalia, C. Prakash and R. S. Jolly, J. Chem. Soc., Perkin Trans. 1, 1981, 1697 DOI: 10.1039/P19810001697

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