Chem. J. Chinese Universities ›› 2001, Vol. 22 ›› Issue (4): 584.
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JIA Yan-Xing, WU Bin, TU Yong-Qiang
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Abstract: Astereoselective synthesis of (3 S,5S,6S )-3,7-dimethyl-5,6-dihydroxy-7-en-octanal, a key intermediate, for the synthesis of the HIVinhibitory didemnaketals analogue, was performed via a series of reactions from the natural(+)-pulegone. In this approach, an interesting and valuable diastereo recognizable reaction between tertiary hydroxyepoxides and PCCwas found. Therefore, the mixture of compounds 8 and 9 was treated with PCCto recover 8 in 93% yield and de 98% purity.
Key words: Spiroketal, R-(+)-Pulegone, Diastereo-recognizable oxidation reaction, 3,7-Dimethyl-5,6-dihydroxy-7-en-octanal intermediate
CLC Number:
O625
TrendMD:
JIA Yan-Xing, WU Bin, TU Yong-Qiang . Synthesis of Chiral Intermediate (3S,5S,6S)-3,7-Dimethyl-5,6-dihydroxy-7-en-octanal of Didemnaketals Analogue[J]. Chem. J. Chinese Universities, 2001, 22(4): 584.
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http://www.cjcu.jlu.edu.cn/EN/Y2001/V22/I4/584