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Issue 30, 2013
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The cascade radical cyclisation approach to prenylated alkaloids: synthesis of stephacidin A and notoamide B

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Abstract

A strategy for the synthesis of members of the prenylated indole alkaloid family is described, which involves a radical cascade process of an appropriately substituted diketopiperazine (DKP) core structure. Several approaches to the generation of the initial radical were explored, with the most successful involving treatment of a sulfenyl substituted DKP under classical reductive conditions by heating with Bu3SnH and a radical initiator. The required, fully substituted, radical precursor DKP structures were prepared using regio- and stereocontrolled enolate chemistry of simpler proline-tryptophan derived DKPs. The new approach allowed rapid access to a key polycyclic indoline structure, which was converted into either of the natural products stephacidin A or notoamide B.

Graphical abstract: The cascade radical cyclisation approach to prenylated alkaloids: synthesis of stephacidin A and notoamide B

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Publication details

The article was received on 08 May 2013, accepted on 13 Jun 2013 and first published on 14 Jun 2013


Article type: Paper
DOI: 10.1039/C3OB40979A
Citation: Org. Biomol. Chem., 2013,11, 4957-4970
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    The cascade radical cyclisation approach to prenylated alkaloids: synthesis of stephacidin A and notoamide B

    N. S. Simpkins, I. Pavlakos, M. D. Weller and L. Male, Org. Biomol. Chem., 2013, 11, 4957
    DOI: 10.1039/C3OB40979A

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