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
APA
Chicago
ICMJE
MLA
NLM
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.
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