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Issue 66, 2014
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Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

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Abstract

A consecutive synthetic strategy was developed toward the total synthesis of securinega alkaloids. (−)-Norsecurinine was concisely assembled by addition of a methoxyallene to a ketone for efficient side-chain installation. Ring-closing metathesis was also utilized as a key step. The first total synthesis of (−)-niruroidine was achieved from (−)-norsecurinine in three steps, while the route to (−)-flueggine A featured a 1,3-dipolar cycloaddition to forge the core structure.

Graphical abstract: Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

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Publication details

The article was received on 08 Apr 2014, accepted on 25 Jun 2014 and first published on 27 Jun 2014


Article type: Communication
DOI: 10.1039/C4CC02575J
Chem. Commun., 2014,50, 9284-9287

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    Total synthesis of securinega alkaloids (−)-norsecurinine, (−)-niruroidine and (−)-flueggine A

    N. Ma, Y. Yao, B. Zhao, Y. Wang, W. Ye and S. Jiang, Chem. Commun., 2014, 50, 9284
    DOI: 10.1039/C4CC02575J

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