An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

Ke Kong; John A. Enquist; Monica E. McCallum; Genessa M. Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L. Wood

doi:10.1021/ja405548b

An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B

Ke Kong, John A. Enquist, Monica E. McCallum, Genessa M. Smith, Takanori Matsumaru, Elnaz Menhaji-Klotz, John L. Wood

Department of Chemistry

Research output: Contribution to journal › Article

48 Citations (Scopus)

Abstract

This manuscript describes an enantioselective synthesis of the naturally occurring alkaloid citrinadin B. The synthetic effort revealed an anomaly in the original structural assignment that has led to the proposal of a stereochemical revision. This revision is consistent with the structures previously reported for a closely related family of alkaloids, PF1270A-C. The synthesis is convergent and employs a stereoselective intermolecular nitrone cyloaddition reaction as a key step.

Original language	English
Pages (from-to)	10890-10893
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	30
DOIs	https://doi.org/10.1021/ja405548b
Publication status	Published - 2013 Jul 31

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Kong, K., Enquist, J. A., McCallum, M. E., Smith, G. M., Matsumaru, T., Menhaji-Klotz, E., & Wood, J. L. (2013). An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. Journal of the American Chemical Society, 135(30), 10890-10893. https://doi.org/10.1021/ja405548b

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10.1021/ja405548b