ARYLLEAD TRIACETATES AS SYNTHONS FOR THE SYNTHESIS OF BIFLAVONOIDS .2. SYNTHESIS OF A GARCINIA-TYPE BIFLAVONOID

Authors
DONNELLY DMX FITZPATRICK BM RYAN SM FINET JP
Citation
Dmx. Donnelly et al., ARYLLEAD TRIACETATES AS SYNTHONS FOR THE SYNTHESIS OF BIFLAVONOIDS .2. SYNTHESIS OF A GARCINIA-TYPE BIFLAVONOID, Journal of the Chemical Society. Perkin transactions. I, (13), 1994, pp. 1797-1801
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
13
Year of publication
1994
Pages
1797 - 1801
Database
ISI
SICI code
0300-922X(1994):13<1797:ATASFT>2.0.ZU;2-Y
Abstract
Arylation of 3-(phenylsulfonyl)chroman-4-one 1 with simple aryllead tr iacetates affords the corresponding 3-aryl-3-(phenylsulfonyl)chroman-4 -one in 64-74% yield. However. no reaction took place with the hindere d 2,4,6-trimethoxyphenyllead triacetate 9. Reaction of the 8-triacetox yplumbyl-flavane derivative 10 with 4'-methoxy-3-(phenylsulfanyl)flava none 11 afforded the biflavanone 12 in 64% yield. Nickel boride reduct ion of compound 12 led to the chalcone 13, which was recyclised to the Garcinia-type (I-3, II-8) biflavanone 14. Dimethyldioxirane oxidation of 12 gave the flavone-flavanone 15.