Sarpagine and Related Alkaloids.
Sarpagine and Related Alkaloids.
复制标题
DOI：
10.1016/bs.alkal.2015.08.002
复制
发表时间：
2016
期刊：
影响因子：
--
通讯作者：
Cook JM
中科院分区：
文献类型：
--
作者：
Namjoshi OA;Cook JM
正如预期的那样，与沙巴碱相关的大分子碱和艾季马林生物碱具有共同的生物合成来源，并具有重要的结构相似之处。这些吲哚生物碱广泛分布于25个植物属中，主要分布在夹竹桃科植物中。据报道，这类天然产品具有非常多样和有趣的生物学特性。对合成化学家和药物化学家来说，分离新的沙拉帕碱相关生物碱以及不对称合成这些结构复杂的分子是非常重要的。本章共收录了115个新分离的与沙巴碱相关的大分子生物碱和艾季马林生物碱，以及它们的理化性质。提出了一种合成这些单体生物碱和双吲哚的通用而有效的策略，其中包括应用不对称Pictet-Spengler反应(>；98%ee)作为关键步骤，因为四环模板易于放大。本章还包括自2000年以来发表的与沙拉帕碱相关的生物碱的合成。
The sarpagine-related macroline and ajmaline alkaloids share a common biosynthetic origin, and bear important structural similarities, as expected. These indole alkaloids are widely dispersed in 25 plant genera, principally in the Apocynaceae family. Very diverse and interesting biological properties have been reported for this group of natural products. Isolation of new sarpagine-related alkaloids as well as the asymmetric synthesis of these structurally complex molecules are of paramount importance to the synthetic and medicinal chemists. A total of 115 newly isolated sarpagine-related macroline and ajmaline alkaloids, along with their physicochemical properties have been included in this chapter. A general and efficient strategy for the synthesis of these monomeric alkaloids, as well as bisindoles has been presented, which involves application of the asymmetric Pictet–Spengler reaction (>98% ee) as a key step because of the ease of scale up of the tetracyclic template. Also included in this chapter are the syntheses of the sarpagine-related alkaloids, published since the year 2000.