Stereoselective Synthesis of the Indole Alkaloids Nitrarine, Nitramidine, and Isomers. A Biomimetic Approach

The Journal of Organic Chemistry
1994.0

Abstract

Starting from tryptamine and dimeric piperidine derivative 8, the synthesis of 4, an immediate precursor in the biosynthesis of the Nitraria alkaloids, was accomplished. Cyclization of this achiral intermediate in aqueous solution produced a mixture of natural nitramidine 17 and one of its stereoisomers. Stereoselective reductions of these iminium salts with several reductors produced nitrarine (1), isonitrarine (2), and two new isomeric Nitraria indole alkaloids.

Knowledge Graph

Similar Paper

Stereoselective Synthesis of the Indole Alkaloids Nitrarine, Nitramidine, and Isomers. A Biomimetic Approach
The Journal of Organic Chemistry 1994.0
Synthesis of Indole Alkaloid Analogues:  Novel Domino Stereoselective Electrophile Addition−Cyclizations of Tryptophan-Derived α-Amino Nitriles
The Journal of Organic Chemistry 2007.0
Synthesis of Notoamide J: A Potentially Pivotal Intermediate in the Biosynthesis of Several Prenylated Indole Alkaloids
The Journal of Organic Chemistry 2010.0
Total Synthesis via Biomimetic Late-Stage Heterocyclization: Assignment of the Relative Configuration and Biological Evaluation of the Nitraria Alkaloid (±)-Nitrabirine
The Journal of Organic Chemistry 2021.0
Total Synthesis of a Pyrroloindoloquinazoline Alkaloid
Organic Letters 2013.0
Synthesis of indole alkaloid analogues containing the novel hexahydropyrrolo[1′,2′,3′:1,9a,9]imidazo[1,2-a]indole skeleton by ring-closing reactions of tryptophan-derived α-amino nitriles
Tetrahedron 2007.0
Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids
Nature Communications 2022.0
Total Synthesis of Homo- and Heterodimeric Bispyrrolidinoindoline Dioxopiperazine Natural Products
Journal of Natural Products 2021.0
Novel dimeric indole alkaloids from Aristotelia australasica. Structural determination and synthesis
The Journal of Organic Chemistry 1987.0
Novel dimeric indole alkaloids from Aristotelia australasica. Structural determination and synthesis
The Journal of Organic Chemistry 1987.0