Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Total Synthesis of (±) -Solavetivone and Aglycone A3. Regio-and Stereo-Selective Birch Reduction of 6, 10-Dimethyl-2-hydroxyspiro [4.5] deca-6, 9-dien-8-one
CHUZO IWATAMINORU YAMADATAKAFUMI FUSAKAKAZUYUKI MIYASHITAAYATSUGU NAKAMURATETSUAKI TANAKATAKAJI FUJIWARAKEN-ICHI TOMITA
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1987 Volume 35 Issue 2 Pages 544-552

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Abstract

Total synthesis of (±) -solavetivone (1), a spirovetivane phytoalexin, was achieved. The metal catalyzed decomposition of the phenolic diazoketone (8) gave the spiro-dienone (6), selective reduction of which afforded the hydroxy-enone (5). The regio-and stereo-selective Birch reduction of 5 provided a high yield of the hydroxy-spiro-enone (9), whose structure was determined by X-ray crystal analysis. Compound 9 was transformed to (±) -1 and the aglycone A3 in several steps.

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© The Pharmaceutical Society of Japan
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