Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid
Publication
, Journal Article
Cooper, AB; Wang, J; Saksena, AK; Girijavallabhan, V; Ashit, KG; Tze-Ming, C; McPhail, AT
Published in: Tetrahedron
June 5, 1992
The absolute configuration of the antifungal antibiotic cercosporamide was established as C-9b-(-)-(S) by correlation with synthetic (+)-8-methylcercosporamide. This was accomplished via conversion of the isoxazole (6) available from (+)-usnic acid. Structure revision of the key isoxazole (6), previously assigned structure (5), is described; some of the 13C-assignments for usnic acid made by previous workers have also been corrected. © 1992.
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Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
June 5, 1992
Volume
48
Issue
23
Start / End Page
4757 / 4766
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
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Cooper, A. B., Wang, J., Saksena, A. K., Girijavallabhan, V., Ashit, K. G., Tze-Ming, C., & McPhail, A. T. (1992). Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid. Tetrahedron, 48(23), 4757–4766. https://doi.org/10.1016/S0040-4020(01)81572-6
Cooper, A. B., J. Wang, A. K. Saksena, V. Girijavallabhan, K. G. Ashit, C. Tze-Ming, and A. T. McPhail. “Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid.” Tetrahedron 48, no. 23 (June 5, 1992): 4757–66. https://doi.org/10.1016/S0040-4020(01)81572-6.
Cooper AB, Wang J, Saksena AK, Girijavallabhan V, Ashit KG, Tze-Ming C, et al. Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid. Tetrahedron. 1992 Jun 5;48(23):4757–66.
Cooper, A. B., et al. “Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid.” Tetrahedron, vol. 48, no. 23, June 1992, pp. 4757–66. Scopus, doi:10.1016/S0040-4020(01)81572-6.
Cooper AB, Wang J, Saksena AK, Girijavallabhan V, Ashit KG, Tze-Ming C, McPhail AT. Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (-)-cercosporamide with (+)-usnic acid. Tetrahedron. 1992 Jun 5;48(23):4757–4766.
Published In
Tetrahedron
DOI
ISSN
0040-4020
Publication Date
June 5, 1992
Volume
48
Issue
23
Start / End Page
4757 / 4766
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 3101 Biochemistry and cell biology
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry