Issue 0, 1979

Constitution of luteone and parvisoflavones-A and -B and synthesis of their methyl ethers and related isoflavones

Abstract

The reaction of 5,7-dihydroxy-2′,4′-dimethoxyisoflavone (7) with 2-methylbut-3-en-2-ol in the presence of BF3–ether affords the 6-(3-methylbut-2-enyl) derivative (13) and its 8-isomer (9). Partial methylation of 7-hydroxy in (13) yields luteone trimethyl ether (15) and subsequent acid cyclisation gives α-isoluteone trimethyl ether (17) derived from natural luteone (3). Cyclodehydrogenation of (13) with DDQ followed by methylation afforded the fully methylated ether (19) of parvisoflavone-B, and the same two steps with (9) yielded the fully methylated ether (21) of parvisoflavone-A.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1979, 279-282

Constitution of luteone and parvisoflavones-A and -B and synthesis of their methyl ethers and related isoflavones

A. C. Jain, A. Kumar and R. C. Gupta, J. Chem. Soc., Perkin Trans. 1, 1979, 279 DOI: 10.1039/P19790000279

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