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Issue 34, 2012
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First total synthesis of dioxepine bastadin 3

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Abstract

The synthesis of dioxepine bastadin 3, a tyrosinetyramine derivative with a dibenzo-1,3-dioxepine scaffold that is rarely present among natural products, is described. The dibenzo-1,3-dioxepine ring was formed early in the sequence and the (E)-2-(hydroxyimino)-N-alkylamide was generated in the last step by oxidation of the 2-amino-N-alkylamide precursor. The presumably biogenetic late-stage ring formation starting from congener bastadin 3 failed. A new synthesis of this alkaloid was also developed. This new route requires a minimal use of protecting groups and the order of the two key steps was reversed relative to the route to dioxepine bastadin 3.

Graphical abstract: First total synthesis of dioxepine bastadin 3

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Publication details

The article was received on 07 May 2012, accepted on 27 Jun 2012 and first published on 29 Jun 2012


Article type: Paper
DOI: 10.1039/C2OB25874A
Citation: Org. Biomol. Chem., 2012,10, 6945-6950
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    First total synthesis of dioxepine bastadin 3

    S. Pérez-Rodríguez, R. Pereira-Cameselle and Á. R. de Lera, Org. Biomol. Chem., 2012, 10, 6945
    DOI: 10.1039/C2OB25874A

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