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 Citations (Scopus)

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 1-(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
StatePublished - 1973

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Alkaloids
Benzylisoquinolines
Methylation
Cyclization
Chlorides
2,9-dimethoxy-3-hydroxypavinane
G 1617

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Alkaloids of the papaveraceae. XX. 2,9-Dimethoxy-3-hydroxypavinane, a new alkaloid from Argemone munita subsp. rotundata. / Coomes, R. Merrill; Falck, J R; Williams, David K.; Stermitz, Frank R.

In: Journal of Organic Chemistry, Vol. 38, No. 21, 1973, p. 3701-3704.

Research output: Contribution to journalArticle

Coomes, R. Merrill ; Falck, J R ; Williams, David K. ; Stermitz, Frank R. / Alkaloids of the papaveraceae. XX. 2,9-Dimethoxy-3-hydroxypavinane, a new alkaloid from Argemone munita subsp. rotundata. In: Journal of Organic Chemistry. 1973 ; Vol. 38, No. 21. pp. 3701-3704.
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AU - Stermitz, Frank R.

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N2 - 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 1-(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.

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