蛇根碱及相关生物碱。
Sarpagine and Related Alkaloids.
作者信息
Namjoshi Ojas A, Cook James M
机构信息
RTI International, Center for Drug Discovery, Research Triangle Park, NC, USA.
University of Wisconsin-Milwaukee, Chemistry Department, Milwaukee, WI, USA.
出版信息
Alkaloids Chem Biol. 2016;76:63-169. doi: 10.1016/bs.alkal.2015.08.002. Epub 2015 Oct 9.
Abstract
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 family Apocynaceae. Very diverse and interesting biological properties have been reported for this group of natural products. Isolation of new sarpagine-related alkaloids and 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 2000.
摘要
与蛇根碱相关的马里灵和阿吗灵生物碱有着共同的生物合成起源，并且如预期的那样，具有重要的结构相似性。这些吲哚生物碱广泛分布于25个植物属中，主要集中在夹竹桃科。据报道，这类天然产物具有非常多样且有趣的生物学特性。对于合成化学家和药物化学家来说，分离新的与蛇根碱相关的生物碱以及不对称合成这些结构复杂的分子至关重要。本章共收录了115种新分离出的与蛇根碱相关的马里灵和阿吗灵生物碱及其物理化学性质。已提出了一种合成这些单体生物碱以及双吲哚的通用且高效的策略，该策略涉及应用不对称Pictet-Spengler反应（对映体过量>98%）作为关键步骤，因为四环模板易于放大。本章还包括了自2000年以来发表的与蛇根碱相关生物碱的合成方法。
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