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
A Short Synthesis of (-)-Deoxoprosophylline
✍ Scribed by Zhu, Jieping; Jourdant, Angélique
- Book ID
- 115469759
- Publisher
- Japan Institute of Heterocyclic Chemistry
- Year
- 2004
- Tongue
- English
- Weight
- 366 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0385-5414
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📜 SIMILAR VOLUMES
An efficient synthesis of (+)-deoxoprosopinine and (À)-deoxoprosophylline was achieved from N-benzyl-N-Boc serine derivatives ( 7) and (7 0 ).
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.
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