Issue 7, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
13 Nov 2017
Accepted
29 Nov 2017
First published
29 Nov 2017

Chem. Commun., 2018,54, 727-730

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, 54, 727 DOI: 10.1039/C7CC07967B

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