Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2
Functionalization of Lupane-3β,28-diyl Diacetate with Chromium(VI) Oxide. Part 2
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用氧化铬 (VI) 官能化 Lupane-3β,28-二乙酸酯第 2 部分。
DOI：
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发表时间：
1997
期刊：
影响因子：
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通讯作者：
J. Protiva
中科院分区：
文献类型：
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作者：
J. Sejbal;J. Klinot;M. Buděšínský;J. Protiva
早前已有报道，用三氧化铬氧化狼烷-3β，28-二乙酸二酯(1)，得到少量在19β和11位官能化的产物(19β-羟基脲-3β，28-二乙酸二酯（3)和11-oxolupane-3β，28-二乙酸二酯(6)），以及随后氧化的产物，21-oxolup-18-烯-3β，28-二乙酸二酯(4)和酸酐(5)。现在，我们通过功能化位置12、16和21确定了进一步的产物(12-羟基-11- oxolupa -12-烯-3β，28-二乙酸二酯(8),12-oxolupa -3β，28-二乙酸二酯（9)，11- oxolupa -12-烯-3β，28-二乙酸二酯（17），21-oxolupa -3β，28-二乙酸二酯（20）和16-oxolupa -3β，28-二乙酸二酯（22）），或转化为其他衍生物后产生。对得到的化合物进行进一步转化，并通过1h NMR、13c NMR和质谱对其结构进行了确证。
Oxidation of lupane-3β,28-diyl diacetate ( 1 ) with chromium trioxide was reported already earlier to give small amounts of products functionalized in position 19β and 11 (19β-hydroxylupane-3β,28-diyl diacetate ( 3 ) and 11-oxolupane-3β,28-diyl diacetate ( 6 )), together with products of subsequent oxidation, 21-oxolup-18-ene-3β,28-diyl diacetate ( 4 ) and anhydride ( 5 ). Now we identified further products, arising by functionalization in positions 12, 16 and 21 (12-hydroxy-11-oxolup-12-ene-3β,28-diyl diacetate ( 8 ), 12-oxolupane-3β,28-diyl diacetate ( 9 ), 11-oxolup-12-ene-3β,28-diyl diacetate ( 17 ), 21-oxolupane-3β,28-diyl diacetate ( 20 ) and 16-oxolupane-3β,28-diyl diacetate ( 22 )), either as such or after conversion into other derivatives. The obtained compounds were further transformed and structure of the prepared derivatives was confirmed by 1 H NMR, 13 C NMR and mass spectroscopy.