✦ LIBER ✦
Conformationally restricted leukotriene antagonists. Modeling and assignment of structure of [(Octahydro-2-oxo-7-tetra-decylidene-2H-1-benzopyran-8-yl)thio]acetic acids
✍ Scribed by John Paolini; Philip M. Weintraub; Jeffrey S. Sabol; David A. Demeter; H.J.R. Weintraub
- Publisher
- Elsevier Science
- Year
- 1990
- Weight
- 323 KB
- Volume
- 3
- Category
- Article
- ISSN
- 0898-5529
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✦ Synopsis
The proton NMR spectrum of the conformationally restricted, leukotriene antagonist thio]acetic acid (2a) did not support a chair-chair conformation for the bicyclic ring system as is usually expected. Molecular mechanics and semi-empirical molecular orbital calculations, on the model compounds ~b and 4_ b, indicated that 3a exists in a chair-boat rather than a chair-chair form. The findings of this computational study were confirmed by a subsequent x-ray analysis.