Regioselective cleavage of the methylenedioxy group: conversion of (-)-austrobailignan-5 to (-)-dihydroguaiaretic acid

1990 ◽  
Vol 55 (5) ◽  
pp. 1427-1429 ◽  
Author(s):  
Koppaka V. Rao ◽  
Sunil K. Chattopadhyay
Keyword(s):  
Methylenedioxy Group

Lignans of western red cedar (Thujaplicata Donn). IX. Plicatinaphthalene

1969 ◽  
Vol 47 (23) ◽  
pp. 4495-4498 ◽  
Author(s):  
Harold MacLean ◽  
B. F. MacDonald
Keyword(s):  
Thin Layer ◽  
Water Soluble ◽  
Hot Water ◽  
Methylenedioxy Group ◽  
Red Cedar ◽  
Naphthoic Acid ◽  
Trimethyl Ether ◽  
Acid Lactone ◽  
Western Red Cedar ◽  
Layer Chromatography

The last of nine lignans detectable by thin-layer chromatography in the hot-water soluble extractives of western red cedar (Thujaplicata Donn) heartwood has been determined as 6-hydroxy-2(hydroxy-methyl)-7-methoxy-4-(3′,4′-dihydroxy-5′-methoxyphenyl)-3-naphthoic acid lactone (plicatinaphthalene 2) by spectrometric methods, by degradation studies of derivatives, and by preparation of its trimethyl ether derivative 3 from dehydroanhydropicropodophyllin by opening of the methylenedioxy group with boron trichloride.

Alkaloids of the Australian Rutaceae: Melicope fareana. I. Isolation of the Constituent Alkaloids

1949 ◽  
Vol 2 (2) ◽  
pp. 249
Author(s):  
JR Price
Keyword(s):  
Rain Forest ◽  
Forest Tree ◽  
Methylenedioxy Group ◽  
The Family

The bark of the rain-forest tree Melicope fareana F. Muell. belonging to the family Rutaceae contains the four alkaloids melicopine (C17H15O5N), melicopidine (C17H15O5N), melicopicine (C18H19O5N), and acronycidine (C15H15O5N). The first three are each present to the extent of about 1 per cent. while the acronycidine content is about 0.1 per cent. About 1 per cent. of lupeol is also present in the bark. The leaves contain melicopine, melicopidine, melicopicine, and the known furanoquinoline alkaloid skimmianine. Melicopine and melicopidine contain two methoxyl groups, a methylimino and a methylenedioxy group. Melicopicine contains four methoxyl groups and a methylimino group.

scholarly journals Cleavage of the methylenedioxy group with sodium methoxide in dimethyl sulfoxide.

1978 ◽  
Vol 26 (10) ◽  
pp. 3113-3116 ◽  
Author(s):  
SHIGERU KOBAYASHI ◽  
MASARU KIHARA ◽  
YOSHINOBU YAMAHARA
Keyword(s):  
Dimethyl Sulfoxide ◽  
Sodium Methoxide ◽  
Methylenedioxy Group

Acridone studies. VII. Mechanistic implications of bromination studies

1969 ◽  
Vol 22 (7) ◽  
pp. 1511 ◽  
Author(s):  
RH Prager ◽  
HM Thredgold
Keyword(s):  
Double Bond ◽  
Methylenedioxy Group ◽  
Ring Strain

The function of alcohols in the addition of bromine to highly oxygenated acridones is discussed, and pathways proposed to explain the structure of the products. The most important factors appear to be the relief of ring strain by addition across a double bond substituted by a methylenedioxy group, and the intermediacy of bromonium ions.

THE ALKALOIDS OF FUMARIACEOUS PLANTS: XXXVI. CORYDALIS THALICTRIFOLIA FRANCH. AND THE CONSTITUTION OF A NEW ALKALOID, THALICTRIFOLINE

1943 ◽  
Vol 21b (6) ◽  
pp. 111-116 ◽  
Author(s):  
Richard H. F. Manske
Keyword(s):  
Methylenedioxy Group ◽  
Methoxy Groups

Corydalis thalictrifolia Franch. has yielded eight alkaloids, four of which, namely, protopine, stylopine, l-corypalmine, and adlumidine, are known bases. The remaining four, thalictrifoline (alkaloid F58) (C21H23O4N), and its dehydro-base, alkaloid F59 (C20H23O4N), and alkaloid F60 (C20H21O3N), are new. The constitution of thalictrifoline has been elucidated. It is corydaline in which the 9:10-methoxy-groups have been replaced by a methylenedioxy-group.

13C nuclear magnetic resonance spectroscopy of methylenedioxy group-containing C19-diterpenoid alkaloids and their derivatives

1980 ◽  
Vol 58 (17) ◽  
pp. 1875-1879 ◽  
Author(s):  
S. William Pelletier ◽  
Naresh V. Mody ◽  
Oliver D. Dailey Jr.
Keyword(s):  
Structure Elucidation ◽  
Nmr Spectra ◽  
Structural Changes ◽  
Single Frequency ◽  
Resonance Spectroscopy ◽  
Diterpenoid Alkaloids ◽  
Methylenedioxy Group ◽  
13C Nuclear Magnetic Resonance ◽  
Self Consistent ◽  
Proton Decoupling

The natural abundance carbon-13 nmr spectra of some methylenedioxy group-containing C19-diterpenoid alkaloids and their derivatives (dictyocarpine, 14-acetyldictyocarpine, dictyocarpinine, 14-dehydrodictyocarpine, 14-dehydrodictyocarpinine, 6-dehydrodictyocarpinine, 6,14-didehydrodictyocarpinine, deltaline (eldeline), deltamine (eldelidine), 6-dehydrodeltamine, delcorine, 6-acetyldelcorine, and 6-dehydrodelcorine) have been determined. Self-consistent assignments of nearly all the resonances in these compounds have been made with the aid of single-frequency off-resonance proton decoupling techniques, additivity relationships, and the effects induced by certain structural changes. Particular attention is directed towards features of the spectra which are most useful for structure elucidation and identification of the C19-diterpenoid alkaloids.

Reactions of lycoctonine alkaloids containing a 7,8-methylenedioxy group with Na in liquid ammonia

1989 ◽  
Vol 25 (4) ◽  
pp. 450-455
Author(s):  
A. S. Narzullaev ◽  
M. S. Yunusov ◽  
E. G. Sirotenko ◽  
Ya. V. Rashkes ◽  
S. S. Sabirov
Keyword(s):  
Liquid Ammonia ◽  
Methylenedioxy Group
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