Synthesis of chiral intermediate (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-octanal of didemnaketals analogue

被引：0

作者：

Jia, YX ^{[1
]}

Wu, B ^{[1
]}

Tu, YQ ^{[1
]}

机构：

[1] Lanzhou Univ, Dept Chem, Natl Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2001年 / 22卷 / 04期

关键词：

spiroketal; R-(+)-pulegone; diastereo-recognizable oxidation reaction; 3,7-dimethyl-5,6-dihydroxy-7-en-octanal; intermediate;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereoselective synthesis of (3S,5S,6S)-3,7-dimethyl-5,6-dihydroxy-7-en-octanal, a key intermediate, for the synthesis of the HIV-inhibitory 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 PCC was found. Therefore, the mixture of compounds 8 and 9 was treated with PCC to recover 8 in 93% yield and de 98% purity.

引用

页码：584 / 586

页数：3

共 6 条

[1] DIDEMNAKETAL-A AND DIDEMNAKETAL-B, HIV-1 PROTEASE INHIBITORS FROM THE ASCIDIAN DIDEMNUM SP
POTTS, BCM
FAULKNER, DJ
CHAN, JA
SIMOLIKE, GC
OFFEN, P
HEMLING, ME
FRANCIS, TA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6321 - 6322
[2] Tu YQ, 1999, CHEM J CHINESE U, V20, P81
[3] Tu YQ, 1999, CHEM J CHINESE U, V20, P587
[4] Tu YQ, 1998, CHEM J CHINESE U, V19, P754
[5] Synthetic studies of didemnaketal analogue - construction of the (+)- and (-)-5,6-dihydroxy-3,7-dimethyl-octanal intermediates
Wang, PZ
Tu, YQ
Yang, L
Dong, CZ
Kitching, W
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (21) : 3789 - 3795
[6] YOSHICK N, 1986, TETRAHEDRON J, V42, P5465

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