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Issue 8, 2015
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Unified approach to prenylated indole alkaloids: total syntheses of (−)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

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Abstract

A unified strategy for the synthesis of congeners of the prenylated indole alkaloids is presented. This strategy has yielded the first synthesis of the natural product (−)-17-hydroxy-citrinalin B as well as syntheses of (+)-stephacidin A and (+)-notoamide I. An enolate addition to an in situ generated isocyanate was utilized in forging a key bicyclo[2.2.2]diazaoctane moiety, and in this way connected the two structural classes of the prenylated indole alkaloids through synthesis.

Graphical abstract: Unified approach to prenylated indole alkaloids: total syntheses of (−)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

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Publication details

The article was received on 03 Jun 2015, accepted on 18 Jun 2015 and first published on 18 Jun 2015


Article type: Edge Article
DOI: 10.1039/C5SC01977J
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Citation: Chem. Sci., 2015,6, 5048-5052
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    Unified approach to prenylated indole alkaloids: total syntheses of (−)-17-hydroxy-citrinalin B, (+)-stephacidin A, and (+)-notoamide I

    E. V. Mercado-Marin and R. Sarpong, Chem. Sci., 2015, 6, 5048
    DOI: 10.1039/C5SC01977J

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