Stereoselective total synthesis of (−)-deoxoprosophylline
✍ Scribed by Apurba Datta; Jalluri S.Ravi Kumar; Subho Roy
- Book ID
- 108371079
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 115 KB
- Volume
- 57
- Category
- Article
- ISSN
- 0040-4020
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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.
Asymmetric syntheses of (-)-deoxoprosophylline from chiral L-N,N -dibenzyl serine (TBDMS) aldehyde is reported. A highly diastereoselective intramolecular reductive amination of v-oxo amino diol is a key step of the present synthesis.
Michael addition of g-amino alcohol 2 to alkynone 3 affords enamine 4, which is converted into cyclic enamine 6 through its bromide 5. Diastereoselective hydrogenation of 6 followed by protection and epimerization provides piperidine 8. Baeyer-Villiger oxidation of 8 and the subsequent deprotection