Chemical and Pharmaceutical Bulletin

Cynanchoside C₂, a New Steroidal Oligoglycoside from Cynanchum caudatum MAX. : Applycation of ¹³C-NMR Spectroscopy to the Structural Elucidation of Plant Glycosides

KEIJI WADA, KOJI HAYASHI, HIROSHI MITSUHASHI, HIDEO BANDO

1979Volume 27Issue 9 Pages 2252-2254
Published: September 25, 1979
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.27.2252

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A new steroidal oligoglycoside, named cynanchoside C₂, was isolated from the rhizome of Cynanchum caudatum MAX. (Asclepiadaceae). The structure of cynanchoside C₂ was elucidated by the application of ¹³C-nuclear magnetic resonance spectroscopy and chemical reactions.

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Intermolecular Photochemical Cycloaddition of 4-Methoxy-2-quinolone with Olefins : A Regioselective Synthesis of 5-Substituted Cyclobuta [c]-2-quinolones

CHIKARA KANEKO, TOSHIHIKO NAITO

1979Volume 27Issue 9 Pages 2254-2256
Published: September 25, 1979
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.27.2254

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Irradiation of 4-methoxy-2-quinolone (IV) in methanol in the presence of substituted ethylenes provided intermolecular addition products. The cycloaddition reaction was shown to be regioselective giving in all cases 5-substituted 3, 6-dihydrocyclobuta [c]-2-quinolones (V). Base treatment of these cycloadducts afforded the corresponding cyclobuta [c]-2-quinolones (VI).

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Stereospecific Synthesis of Codeine 7, 8-Oxide and Codeinone 7, 8-Oxide

KIYOKO UBA, NAOKI MIYATA, KEIZO WATANABE, MASAAKI HIROBE

1979Volume 27Issue 9 Pages 2257-2258
Published: September 25, 1979
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.27.2257

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Condeinone (1) was oxidized to codeinone 7, 8-oxide (2) by hydrogen peroxide. Stereospecific reduction of 2 by sodium borohydride afforded codeine 7, 8-oxide (3). The configuration of 3 was confirmed by X-ray analysis.

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New Derivatization of Amines for Electrochemical Detection in Liquid Chromatography

KAZUTAKE SHIMADA, MAKOTO TANAKA, TOSHIO NAMBARA

1979Volume 27Issue 9 Pages 2259-2260
Published: September 25, 1979
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.27.2259

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New derivatization of primary and secondary amines for electrochemical detection in liquid chromatography has been developed. The derivatization reagents were prepared from vanillic acid and homovanillic acid by condensation with N-hydroxysuccinimide. Of the two reagents the activated ester of homovanillic acid reacted more readily with amines, providing the amides which were highly responsible for an electrochemical detector in reversed phase chromatography. The detection and quantitation limits determined with ethyl phenylalaninate were 200 pg and 1 ng, respectively.

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