Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.

Chemical and Pharmaceutical Bulletin
1987.0

Abstract

The structure of oxyterihanine (2c), a new phenolic benzo[c]phenanthridone alkaloid which was isolated from Formosan Xanthoxylum nitidum (roxb.) d. c.(Fagara nitida roxb.), was established as 8-hydroxy-9-methoxy-5-methyl-2,3-methylenedioxybenzo[c]phenanthridin-6(5H)-one by direct comparison with a synthetic specimen, which was derived from 2-(4-isopropoxy-3-methoxyphenyl)-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one (8a) through the synthetic sequence shown in Charts 3 and 4. 9-Hydroxy-8-methoxy-5-methyl-2,3-methylenedioxybenzo[c]phenanthridin-6(5H)-one [oxyisoterihanine (2d)] and two phenolic quaternary benzo[c]phenanthridine alkaloids, terihanine (1c) and isoterihanine (1d), were also synthesized. © 1987, The Pharmaceutical Society of Japan. All rights reserved.

Knowledge Graph

Similar Paper

Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.
Chemical and Pharmaceutical Bulletin 1987.0
Alkaloids from the stem bark of an Australian population ofZanthoxylum ovalifolium
Natural Product Research 2006.0
Two New Benzophenanthridine Alkaloids from Zanthoxylum nitidum
Helvetica Chimica Acta 2008.0
A New Benzophenanthridine Alkaloid from Zanthoxylum nitidum
Chinese Journal of Natural Medicines 2009.0
365. An examination of the rutaceae of Hong Kong. Part II. The alkaloids, nitidine and oxynitidine, from Zanthoxylum nitidum
Journal of the Chemical Society (Resumed) 1959.0
Two New Benzophenanthridine Alkaloids from <i>Zanthoxylum nitidum</i>
Helvetica Chimica Acta 2008.0
A New Benzophenanthridine Alkaloid from &lt;I&gt;Zanthoxylum nitidum&lt;/I&gt;
Chinese Journal of Natural Medicines 2009.0
Ailanthoidine, a novel benzo(C)phenanthridine alkaloid with a cyanopyridine pendant, from a Xanthoxylum species.
Chemical and Pharmaceutical Bulletin 1991.0
Studies on the Chemical Constituents of Rutaceous Plants. XLVIII. The Chemical Constituents of Xanthoxylum ailanthoides SIEB. et ZUCC. [Fagara ailanthoides (SIEB. et ZUCC.) ENGL.]. (3) Isolation of the Chemical Constituents of the Bark
YAKUGAKU ZASSHI 1983.0
(R)-(+)-Isotembetarine, a Quaternary Alkaloid from Zanthoxylum nitidium
Journal of Natural Products 1997.0