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Sarpagine and Related Alkaloids. Alkaloids Chem Biol 2016;76:63-169

Date

02/02/2016

Pubmed ID

26827883

Pubmed Central ID

PMC4864735

DOI

10.1016/bs.alkal.2015.08.002

Scopus ID

2-s2.0-84978621469 (requires institutional sign-in at Scopus site)   52 Citations

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.

Author List

Namjoshi OA, Cook JM

Author

James M. Cook PhD University Distinguished Professor in the Chemistry and Biochemistry department at University of Wisconsin - Milwaukee




MESH terms used to index this publication - Major topics in bold

Ajmaline
Indole Alkaloids
Magnetic Resonance Spectroscopy
Secologanin Tryptamine Alkaloids