TY - JOUR
T1 - Alkaloids of the Papaveraceae. XX. 2,9-Dimethoxy-3-hydroxypavinane, a New Alkaloid from Argemone munita subsp. rotundata
AU - Coomes, R. Merrill
AU - Falck, J R
AU - Williams, David K.
AU - Stermitz, Frank R.
PY - 1973/10/1
Y1 - 1973/10/1
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 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.
AB - 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.
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U2 - 10.1021/jo00961a009
DO - 10.1021/jo00961a009
M3 - Article
C2 - 4745877
AN - SCOPUS:0015930221
SN - 0022-3263
VL - 38
SP - 3701
EP - 3704
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -