13C-nuclear magnetic resonance spectra of oxiranes. Configuration of 1,2-epoxypropyl side chains in fungal metabolites
- 15 December 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (24) , 3117-3120
- https://doi.org/10.1139/v78-509
Abstract
13C nmr data indicate that the epoxypropyl side chain of 'asperlin' (1) has a trans configuration. This assignment follows from associated measurements on model compounds, showing that the 13C chemical shift of an epoxypropyl CH3 group is close to either 17 ppm (trans isomers) or 13 ppm (cis isomers). Synthesized as oxirane derivatives related to 1 are diastereomeric pairs of 8-deoxy-6,7-cis- and -trans-epoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octopyranoses.Keywords
This publication has 1 reference indexed in Scilit:
- Synthesis and stereochemistry of 2-pyrone derivatives related to some fungal metabolitesCanadian Journal of Chemistry, 1978