Total synthesis of (-)-verruearol (1) was achieved starling from D-glucose-derived bicyclic lactone 4 through l) a stereoselective asymmetric quatemization of the a-carbon of the lactone, 2) Dieckmann cyclization for access to the C-ring equivalent, 3) a skeletal rearrangement for the trichothecene
Synthesis of tritium labelled verrucarol and verrucarin a
β Scribed by Boris Yagen; Bruce B. Jarvis
- Publisher
- John Wiley and Sons
- Year
- 1989
- Tongue
- French
- Weight
- 332 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0022-2135
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β¦ Synopsis
Two tritium labelled trichothecenes, vermcarol(2) and verrucarin A (5) were synthesized with high specific activity. Oxidation of vermcarol(1) to the 15dehydrovermcarol(3) followed by sodium borotritide reduction yielded [ W3H]vermcarol(2). Reduction of 16mesyloxyvermcarin A (7) in a special bufferorganic solvent system with a phase transfer catalyst, produced [16-3H]vermcarin A (5). Final purification of the radioactive products was achieved by preparative thin layer chromatography. Their structures were assigned based on the analytical data of the corresponding nonradiolabelled compounds obtained from the nonradioactive preparations.
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