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Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions

Publication ,  Journal Article
Baldwin, SW; McPhail, AT; Aubé, J
Published in: Journal of Organic Chemistry
November 1, 1991

A protocol for the synthesis of optically active pretazettine which focuses on both the control of relative stereochemistry between the angular aryl and C6a hydroxyl groups and absolute stereochemistry has been developed and executed. The synthesis of the 1,3-dithiane ketal of (Z)-ethyl 3-(1,3-benzodioxol-5-yl)-5,7-dioxo-2-heptanoate is described. Treatment of this alkene aldehyde with N-(α-methylbenzyl)hydroxylamine afforded a nitrone, which underwent intramolecular 1,3-dipolar cycloaddition to afford the two diastereomeric isoxazolidine cycloadducts in a 16:1 ratio. The sense of chirality transfer was determined by a single-crystal X-ray analysis of the major isomer. © 1991, American Chemical Society. All rights reserved.

Duke Scholars

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

November 1, 1991

Volume

56

Issue

23

Start / End Page

6546 / 6550

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Baldwin, S. W., McPhail, A. T., & Aubé, J. (1991). Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions. Journal of Organic Chemistry, 56(23), 6546–6550. https://doi.org/10.1021/jo00023a019
Baldwin, S. W., A. T. McPhail, and J. Aubé. “Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions.” Journal of Organic Chemistry 56, no. 23 (November 1, 1991): 6546–50. https://doi.org/10.1021/jo00023a019.
Baldwin SW, McPhail AT, Aubé J. Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions. Journal of Organic Chemistry. 1991 Nov 1;56(23):6546–50.
Baldwin, S. W., et al. “Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions.” Journal of Organic Chemistry, vol. 56, no. 23, Nov. 1991, pp. 6546–50. Scopus, doi:10.1021/jo00023a019.
Baldwin SW, McPhail AT, Aubé J. Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions. Journal of Organic Chemistry. 1991 Nov 1;56(23):6546–6550.
Journal cover image

Published In

Journal of Organic Chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

November 1, 1991

Volume

56

Issue

23

Start / End Page

6546 / 6550

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry