Author:
Clark-Lewis JW,Jemison RW
Abstract
Further applications of flav-3-enes for synthesis of flavan
derivatives are reported, with discussion of stereochemical aspects.
Hydrogenation of three 3-sub-stituted flav-3-enes gave the corresponding 2,3-cis-flavans, viz. (�)-epiafzelechin
tetramethyl ether, and (�)-epicatechin
pentamethyl ether and pentaacetate.
Hydroxylation of 5,7,3',4'-tetramethoxyflav-3-ene with osmium tetroxide
gave 5,7,3',4'-tetramethoxy-2,3-trans-flavan-3,4-cis-diol.
The trans-trans isomer of this diol
proved configurationally unstable towards hot acetic anhydride and sodium
acetate, and gave the 2,3-trans-3,4-cis diacetate in addition to the normal trans-trans diacetate. Two 2,4-cis-flavan-4-01s
were found to give 2,4-trans-4-ethoxyflavans, and thus resembled flavan-3,4-diols in their solvolytic
reaction with ethanol.
Meerwein-Ponndorf reduction of flavanone
gave 2,4-cis-flavan-4-ol
(i.e. the quasi-equatorial alcohol).
Cited by
8 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
1. Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives;Journal of Chemistry;2017
2. A convenient method for conversion of flavonols into anthocyanins;Tetrahedron Letters;1995-06
3. Chemical and enzymatic synthesis of monomeric procyanidins (leucocyanidins or 3′,4′,5,7-tetrahydroxyflavan-3,4-diols) from (2R,3R)-dihydroquercetin;Phytochemistry;1985-02
4. Synthesis and reactions of 4-aryloxyflavans;Journal of the Chemical Society, Perkin Transactions 1;1983
5. Leucocyanidin: Synthesis and properties of (2R,3S,4R)-(+)-3,4,5,7,3′,4′-hexahydroxyflavan;Phytochemistry;1980-01