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Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(I)-catalyzed asymmetric enyne cycloisomerization

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Abstract

A diversity-oriented synthetic strategy was developed for the total synthesis of kainoid amino acids, which led to the enantioselective synthesis of (−)-kainic acid and the first total synthesis of (+)-acromelic acid C. Rh(I)-catalyzed asymmetric enyne cycloisomerization served as the key reaction in this strategy for the rapid construction of highly functionalized lactam, and the resulting vinyl acetate moiety was further utilized as a versatile building block for the installation of both isopropylidene and 2-pyridone units existing in natural kainoids.

Graphical abstract: Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(i)-catalyzed asymmetric enyne cycloisomerization

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Publication details

The article was received on 13 Nov 2017, accepted on 29 Nov 2017 and first published on 29 Nov 2017


Article type: Communication
DOI: 10.1039/C7CC07967B
Citation: Chem. Commun., 2018, Advance Article
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    Enantioselective total synthesis of (−)-kainic acid and (+)-acromelic acid C via Rh(I)-catalyzed asymmetric enyne cycloisomerization

    H. Lei, S. Xin, Y. Qiu and X. Zhang, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC07967B

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