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Asymmetric total synthesis of (−)-deoxoprosophylline

✍ Scribed by Angélique Jourdant; Jieping Zhu

Book ID
104230551
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
72 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Asymmetric synthesis of (−)-deoxoprosoph
Asymmetric synthesis of (−)-deoxoprosophylline
✍ Nan Ma; Dawei Ma 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 210 KB

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