title: The Rhazinilam-Leuconoxine-Mersicarpine Triad of Monoterpenoid Indole Alkaloids.
abstract: The rhazinilam-leuconoxine-mersicarpine triad of monoterpenoid indole alkaloids comprises a variety of diverse natural products with unprecedented structural features and intriguing biological activities. This subfamily of Aspidosperma alkaloids has drawn significant attention from the synthetic community which is reflected by over 20 syntheses within the last 5years. Numerous transformations and strategies have been developed to access the different key structural motifs such as the tetrahydroindolizine, α,β-unsaturated carbinolamide, diaza[5.5.6.6]fenestrane, and tetrahydro-2H-azepine frameworks. The present contribution comprehensively covers the abundant literature on this natural product class up to the end of May 2016, providing a detailed account of the formal and total syntheses which is complemented by an overview of their biosynthesis, spectroscopy, and pharmacology.
authors.affiliation: University of Konstanz, Konstanz, Germany.
authors.forename: Magnus
authors.initials: M
authors.lastname: Pfaffenbach
authors.affiliation: University of Konstanz, Konstanz, Germany.
authors.forename: Tanja
authors.initials: T
authors.lastname: Gaich
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D029062:Apocynaceae / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis / Q000737:chemistry; D007769:Lactams / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D000470:Alkaloids; D026121:Indole Alkaloids; D007212:Indolizines; D007769:Lactams; C000590191:leuconoxine; C529544:mersicarpine; C009170:rhazinilam
keywords: Indole alkaloid; Leuconolam; Leuconoxine; Mersicarpine; Natural product; Polycyclic; Rhazinilam; Total synthesis