Alkaloids of the Papaveraceae. XX. 2,9-Dimethoxy-3-hydroxypavinane, a New Alkaloid from Argemone munita subsp. rotundata

R. Merrill Coomes, J R Falck, David K. Williams, Frank R. Stermitz

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

A new alkaloid (C19H21NO3, mp 197-198°, [α]27D −254°) was isolated from Argemone munita Dur. & Hilg. subsp. rotundata (Rydb.) G. B. Owmb. and was shown to be 2,9-dimethoxy-3-hydroxypavinane (I) by total synthesis. The synthesis was accomplished by formation of the Reissert compound from 7-methoxyisoquinoline and 3-methoxy-4-benzyloxybenzyl chloride, conversion to the benzylisoquinoline, N-methylation, reduction to the 1,2-dihydroisoquinoline, and cyclization to I with HCOOH and H3PO4. If the latter three steps were carried out on l-(4-methoxybenzyl)-6,7-dimethoxyisoquinoline, the final product under the HCOOH and H3PO4 conditions was not a pavinane alkaloid, but instead the rearranged product 3-(4-methoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-N-methylisoquinoline.

Original languageEnglish (US)
Pages (from-to)3701-3704
Number of pages4
JournalJournal of Organic Chemistry
Volume38
Issue number21
DOIs
StatePublished - Oct 1 1973

ASJC Scopus subject areas

  • Organic Chemistry

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