✦ LIBER ✦

An unusual carbon to nitrogen acyl migration

✍ Scribed by Jerome L. Moniot; el Rahman H. Abd; Abd el Rahman; Maurice Shamma

Book ID: 104235651
Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 199 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)83354-2

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✦ Synopsis

The known ylide 8-methoxyberberinephenolbetaine (2a) may be obtained either by ferricyanide oxidation 3 or by photolysis of berberine (AI. 4 The unmasking of the potential carboxylic ester at C-8 by hydration in wet ether, a solvent in which it is only slightly soluble, has been shown to furnish the enamine 3. Subsequent N-methylation and reduction of 2 affords a mixture of the phthalideisoquinolines(i)-U. and (*)-,3-hydrastine. 3

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