The synthesis of nor- and bisnorlupanes
The synthesis of nor- and bisnorlupanes
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DOI：
10.1139/v91-086
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发表时间：
1991-03
影响因子：
1.1
通讯作者：
A. Wahhab;M. Ottosen;F. W. Bachelor
中科院分区：
文献类型：
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作者：
A. Wahhab;M. Ottosen;F. W. Bachelor
在地球化学生物标志物的研究过程中，我们需要一系列的狼烷标准。我们在这里报道了从桦木素(3)中三步合成狼烷(1)的有效方法，总收率为47.2%。17β(H)-28-Norlupane(2)纯度为90%，采用Barton方法对3-oxolupan-28-oic酸进行脱羧（10）。24,28-双诺环烷(4)和24-诺环烷(5)是通过一系列反应得到的，包括肟、二腈、环氧腈的形成、环闭合，最后是C3羰基的Wolff-Kishner还原为亚甲基。此外，为了帮助从油页岩和地质样品中定量测定这些lupanes，需要3- deuteruupane(6)和2,3- dideuteruupane(7)，并报道了它们的制备方法。关键词：狼烷，24-去甲狼烷，28-去甲狼烷，24,28-二去甲狼烷，3-二叔狼烷，2,3-二叔狼烷
In the course of our studies on geochemical biomarkers we required a series of lupane standards. We report here an efficient synthesis of lupane (1) in three steps from betulin (3) in an overall yield of 47.2%. 17β(H)-28-Norlupane (2) was obtained in 90% purity employing Barton's method for the decarboxylation of 3-oxolupan-28-oic acid (10). 24,28-Bisnorlupane (4) and 24-norlupane (5) were obtained by a series of reactions involving formation of the oxime, the seconitrile, the epoxynitrile, ring closure, and finally a Wolff–Kishner reduction of the C3 carbonyl to the methylene. Also, to aid in the quantitative determination of these lupanes from oil shales and geological samples, 3-deuterolupane (6) and 2,3-dideuterolupane (7) were needed, and a method for their preparation is reported. Key words: lupane, 24-norlupane, 28-norlupane, 24,28-bisnorlupane, 3-deuterolupane, 2,3-dideuterolupane.