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Indole Prenylation in Alkaloid Synthesis

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Book cover Alkaloid Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 309))

Abstract

Important biologically active indole alkaloids are decorated with prenyl (3,3-dimethylallyl) and tert-prenyl (1,1-dimethylallyl) groups. Covering the literature until the end of 2010, this review article comprehensively summarises and discusses the currently available technologies of prenylation and tert-prenylation of indoles, which have been applied in natural products total syntheses or could be applied there in the near future. We focus on those procedures which introduce the C5 units in one step, organised according to the indole position to be functionalised. Key strategies include electrophilic and nucleophilic prenylation and tert-prenylation, prenyl and tert-prenyl rearrangements, transition metal-mediated reactions and enzymatic methods.

Dedicated to Professor Gerhard Bringmann on the occasion of his 60th birthday.

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  1. Institut für Organische Chemie, TU Braunschweig, Hagenring 30, 38106, Braunschweig, Germany

    Thomas Lindel, Nils Marsch & Santosh Kumar Adla

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  1. Thomas Lindel
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  1. , Department Chemie, Technische Universität Dresden, Bergstrasse 66, Dresden, 01069, Germany

    Hans-Joachim Knölker

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Lindel, T., Marsch, N., Adla, S.K. (2011). Indole Prenylation in Alkaloid Synthesis. In: Knölker, HJ. (eds) Alkaloid Synthesis. Topics in Current Chemistry, vol 309. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2011_204

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