4.4 Article

A Bidirectional Synthesis of (+)-Terreusinone

Journal

SYNLETT
Volume -, Issue 12, Pages 1824-1828

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0031-1290693

Keywords

terreusinone; pyrroloindole; Sonogashira coupling; hydroamination; natural product

Funding

  1. Royal Society of New Zealand Marsden Fund

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An efficient, bidirectional synthesis of the photoprotecting dipyrrolobenzoquinone (+)-terreusinone has been accomplished. Key steps include a copper-and amine-free double Sonogashira reaction of an electron-rich 1,4-dibromide with a protected propargylic alcohol followed by pyrrolo[2,3-f]indole formation by double hydroamination catalyzed by Echavarren's cationic gold(I) complex. This new route to (+)-terreusinone complements the original synthesis and offers advantages over its predecessor.

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