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Issue 1, 2016
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Concise synthesis of (+)-fastigiatine

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Abstract

(+)-Fastigiatine was assembled in six steps from (R)-5-methylcyclohex-2-en-1-one. Intermolecular Diels–Alder reaction introduced most of the carbon atoms for the target. The two Boc-protected nitrogen atom building blocks were introduced by a Suzuki coupling and a cuprate addition. A biomimetic transannular Mannich reaction generated the two quaternary centers at a late stage. Each step builds core bonds, and combined with a minimalist protecting group strategy, this approach led to a very concise synthesis.

Graphical abstract: Concise synthesis of (+)-fastigiatine

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Publication details

The article was received on 31 Aug 2015, accepted on 25 Sep 2015 and first published on 06 Oct 2015


Article type: Edge Article
DOI: 10.1039/C5SC03262H
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Chem. Sci., 2016,7, 188-190
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    Concise synthesis of (+)-fastigiatine

    R. A. Samame, C. M. Owens and S. D. Rychnovsky, Chem. Sci., 2016, 7, 188
    DOI: 10.1039/C5SC03262H

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