Furanocembranolide interconversions. Transformation of pseudopterolide into tobagolide and its reversal
✍ Scribed by Leo A. Paquette; Peter C. Astles
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- French
- Weight
- 199 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Pseudopterolide is efficiently transformed into tobagolide by reaction with dimethylamine. Sequential treatment of tobagolide with methyl iodide and sodium hydride results in intramolecular SD'displacement with reconstruction of pseudopterolide. The gorgonian corals of the genus Pseudopterogorgia have become recognized as important sources of a small class of structurally complex 12-membered furanocembranolides valued for their cytotoxic and anti-inflammatory properties. Following the original characterization of pseudopterolide (1) in 1982,l Fenical subsequently identified kallolide A (2a) and kallolide B (2b) as lesser oxygenated analogues.2 More recently, Chan, NcLean, and their co-workers reported on the isolation of tobagolide (3a), the first from P. acerosa in the month of J~ly.~ The presence of 3a 73 ,C4% nitrogenous pseudopterane, /CWHa