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| Content Provider | Royal Society of Chemistry (RSC) |
|---|---|
| Author | Horibe, Isao Yoshioka, Hirosuke Mabry, Tom J. Tori, Kazuo |
| Copyright Year | 1971 |
| Abstract | The conformations of the two conformational isomers of isabelin (1), a germacranolide dilactone isolated from Ambrosia psilostachya DC. (Compositae), have been determined in chloroform solution by use of the intramolecular nuclear Overhauser effect; and further, the configuration of the endocyclic double-bond in its ten-membered ring has been confirmed. It has been concluded that the major and minor isomers of isabelin mainly adopt the conformations (A) and (B), respectively, which have a trans-orientation of the endocyclic double-bond. Since isabelin has been correlated with artemisiifolin (3), salonitenolide (4), and cnicin (5), the results obtained here have also established a trans configuration for these three germacranolide monolactones. In addition, isoisabelin (2), a geometrical isomer of isabelin, has been examined to determine the configuration of its C(9)–C(10) double-bond and its conformation. |
| Starting Page | 1084 |
| Ending Page | 1088 |
| Page Count | 5 |
| File Format | |
| ISSN | 00456470 |
| Volume Number | 0 |
| Journal | Journal of the Chemical Society B: Physical Organic |
| DOI | 10.1039/J29710001084 |
| Language | English |
| Publisher | Royal Society of Chemistry |
| Access Restriction | Open |
| Subject Keyword | Germacranolide Lactone Ambrosia psilostachya Asteraceae Chloroform Cnicin Isomer Conformational isomerism |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Physical and Theoretical Chemistry |
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