✦ LIBER ✦

Asymmetric synthesis of (−)-deoxoprosophylline

✍ Scribed by Nan Ma; Dawei Ma

Book ID: 104359826
Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 210 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00275-1

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✦ Synopsis

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 give (-)-deoxoprosophylline.

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