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

Research output: Contribution to journal › Article

47 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 languageEnglish
Pages (from-to)10890-10893
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number30
DOIs
Publication statusPublished - 2013 Jul 31
Externally publishedYes

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Alkaloids
citrinadin A
nitrones
PF1270A

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

An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. / Kong, Ke; Enquist, John A.; McCallum, Monica E.; Smith, Genessa M.; Matsumaru, Takanori; Menhaji-Klotz, Elnaz; Wood, John L.

In: Journal of the American Chemical Society, Vol. 135, No. 30, 31.07.2013, p. 10890-10893.

Research output: Contribution to journal › Article

Kong, K, Enquist, JA, McCallum, ME, Smith, GM, Matsumaru, T, Menhaji-Klotz, E & Wood, JL 2013, 'An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B', Journal of the American Chemical Society, vol. 135, no. 30, pp. 10890-10893. https://doi.org/10.1021/ja405548b
Kong K, Enquist JA, McCallum ME, Smith GM, Matsumaru T, Menhaji-Klotz E et al. An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. Journal of the American Chemical Society. 2013 Jul 31;135(30):10890-10893. https://doi.org/10.1021/ja405548b
Kong, Ke ; Enquist, John A. ; McCallum, Monica E. ; Smith, Genessa M. ; Matsumaru, Takanori ; Menhaji-Klotz, Elnaz ; Wood, John L. / An enantioselective total synthesis and stereochemical revision of (+)-citrinadin B. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 30. pp. 10890-10893.
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