The structure and synthesis of fadyenolide, a new butemolide from piper fadyenii

✍ Scribed by Andrew Pelter; Redha AI-Bayati; Rudolf Ha̋nsel; Hildegard Dinter; Basil Burke

• Publisher: Elsevier Science
• Year: 1981
• Tongue: French
• Weight: 200 KB
• Volume: 22
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)90373-9

✦ Synopsis

The isolation, structure and synthesis of 5,6-Z-and E-fadyenolides, the simplest -butenolides of the piperolide series, are reported.

We have previously shown that Piper sanctum from Mexico, contains a series of 4-methoxybutenolides (methyl tetronates) with further exocyclic conjugation extending from c-5. These compounds are all related to 5,6-L-piperolide (l), the structure of which is certain based on physical data, 1 X-ray analysis* and synthesis.

3 Up to now these compounds represent the only butenolides derived from higher plants and are probably produced by a unique biosynthetic process involving the rearrangement of suitably substituted dihydro-pyrones4 with which they co-occur.