Abstract
The synthetic efforts of the authors research team in several areas within the monoterpene indole alkaloid family are summarized. Most of the work was accomplished in the field of the Aristotelia alkaloids, where some 25 natural products were synthesized for the first time. Systematic investigations on the oxidative rearrangement of indoles to oxindoles and pseudoindoxyl derivatives led to control over the chemoselectivity and stereoselectivity of this process, which served for enantioselective preparations of the simple alkaloids horsfiline and elacomine. In addition, recent developments in a novel approach to Iboga alkaloids containing a hydroxyl group at C(19) are presented. The key steps involved a self-immolating 1,4-chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone-olefin [2+3]-cycloaddition to give the aliphatic isoquinuclidine core of the target molecules. The first synthesis of (19R)- hydroxyibogamine was completed by grafting a 3-ethylindole unit onto the aliphatic nitrogen, followed by closing the 7- membered ring.
Keywords: aristotelia alkaloids, aza-adamantane, indole-protected aristofruticosine, elaeagnus commutata, dreiding models, corynanthine
Current Organic Chemistry
Title: New Strategies for the Synthesis of Monoterpene Indole Alkaloids
Volume: 9 Issue: 15
Author(s): Hans-Jurg Borschberg
Affiliation:
Keywords: aristotelia alkaloids, aza-adamantane, indole-protected aristofruticosine, elaeagnus commutata, dreiding models, corynanthine
Abstract: The synthetic efforts of the authors research team in several areas within the monoterpene indole alkaloid family are summarized. Most of the work was accomplished in the field of the Aristotelia alkaloids, where some 25 natural products were synthesized for the first time. Systematic investigations on the oxidative rearrangement of indoles to oxindoles and pseudoindoxyl derivatives led to control over the chemoselectivity and stereoselectivity of this process, which served for enantioselective preparations of the simple alkaloids horsfiline and elacomine. In addition, recent developments in a novel approach to Iboga alkaloids containing a hydroxyl group at C(19) are presented. The key steps involved a self-immolating 1,4-chirality transfer in an Ireland-Claisen rearrangement and an intramolecular nitrone-olefin [2+3]-cycloaddition to give the aliphatic isoquinuclidine core of the target molecules. The first synthesis of (19R)- hydroxyibogamine was completed by grafting a 3-ethylindole unit onto the aliphatic nitrogen, followed by closing the 7- membered ring.
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Cite this article as:
Borschberg Hans-Jurg, New Strategies for the Synthesis of Monoterpene Indole Alkaloids, Current Organic Chemistry 2005; 9 (15) . https://dx.doi.org/10.2174/138527205774370522
DOI https://dx.doi.org/10.2174/138527205774370522 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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