title: Sarpagine and Related Alkaloids.
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.
authors.affiliation: RTI International, Center for Drug Discovery, Research Triangle Park, NC, USA.
authors.forename: Ojas A
authors.initials: OA
authors.lastname: Namjoshi
authors.affiliation: University of Wisconsin-Milwaukee, Chemistry Department, Milwaukee, WI, USA.
authors.forename: James M
authors.initials: JM
authors.lastname: Cook
mesh_terms: D000404:Ajmaline / Q000096:biosynthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D046948:Secologanin Tryptamine Alkaloids / Q000737:chemistry / Q000378:metabolism*
chemical_list: D026121:Indole Alkaloids; D046948:Secologanin Tryptamine Alkaloids; D000404:Ajmaline; C475809:sarpagine
keywords: Ajmaline; Biosynthesis; Enantioselective; Macroline; Nature-inspired; Pictet–Spengler reaction; Sarpagine
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