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Issue 26, 2010
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A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

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Abstract

A concise, enantioselective synthesis of the Phase I anticancer agent, (−)-salinosporamide A, is described. The brevity of the described strategy stems from a key bis-cyclization of a β-keto tertiary amide, accomplished on gram scale, which retains optical purity enabled by A1,3-strain rendering epimerization slow relative to the rate of bis-cyclization. The versatility of the strategy for derivative synthesis is demonstrated by the synthesis of (−)-homosalinosporamide A.

Graphical abstract: A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

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Publication details

The article was received on 26 Mar 2010, accepted on 22 Apr 2010 and first published on 25 May 2010


Article type: Communication
DOI: 10.1039/C0CC00607F
Citation: Chem. Commun., 2010,46, 4803-4805
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    A1,3-strain enabled retention of chirality during bis-cyclization of β-ketoamides: total synthesis of (−)-salinosporamide A and (−)-homosalinosporamide A

    H. Nguyen, G. Ma and D. Romo, Chem. Commun., 2010, 46, 4803
    DOI: 10.1039/C0CC00607F

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