Biosynthesis of Lycopodine. The Question of the Intermediacy of Piperidine-2-acetic Acid

1975 ◽  
Vol 53 (1) ◽  
pp. 41-50 ◽  
Author(s):  
W. D. Marshall ◽  
T. T. Nguyen ◽  
D. B. MacLean ◽  
Ian D. Spenser
Keyword(s):  
Acetic Acid ◽  
Malonic Acid ◽  
Pipecolic Acid

In Lycopodiumtristachyum lycopodine is derived from L-lysine whereas pipecolic acid is derived from D-lysine. Malonic acid serves as a specific precurser of the non-lysine derived segments of lycopodine. Piperidine-2-acetic acid is not incorporated into the alkaloid.

Versuche zur Oxidation von 1.5-Benzothiazepin — bzw. 1.5-Benzoxazepin- 2.4-3H.5H-dionen / Investigations Concerning Oxidation Reactions of 1,5-Benzthiazepin — and 1,5-Benzoxazepin- 2,4-3H,5H -diones

1984 ◽  
Vol 39 (3) ◽  
pp. 384-389 ◽  
Author(s):  
G. Kollenz ◽  
P. Seidler
Keyword(s):  
Acetic Acid ◽  
Malonic Acid ◽  
Reaction Pathway ◽  
Simple Synthesis ◽  
Oxidation Reactions ◽  
Acetic Acid Lead ◽  
Malonic Acid Derivatives

Attempts to oxidize the 1,5-benzothiazepin-2,4-3H,5H-dione (1) using NaNO2/Acetic acid lead to isolation of two ring contracted products, namely the 1,4-benzthiazin-derivatives 4 and 5. A reasonable reaction pathway concerning the formation of these compounds is discussed. A simple synthesis of 6-methyI-1,5-benzoxazepin-2,4-3H,5H-dione (13) is described, the transformation of which into the corresponding vic. trione fails, even using a great number of oxidizing procedures. In some cases so far unknown malonic acid derivatives 14, 15 and 16 can be obtained.

PREPARATION OF CAFFEIC AND DIHYDROCAFFEIC ACIDS BY METHODS SUITABLE FOR INTRODUCTION OF C14 INTO THE β-POSITION

1959 ◽  
Vol 37 (12) ◽  
pp. 1431-1438 ◽  
Author(s):  
A. C. Neish
Keyword(s):  
Acetic Acid ◽  
Benzoic Acid ◽  
Caffeic Acid ◽  
Malonic Acid ◽  
Cinnamic Acid ◽  
Catalytic Hydrogenation ◽  
Benzoyl Chloride ◽  
Protocatechuic Acid ◽  
Barium Carbonate ◽  
Hydrogen Bromide

3,4-(Dibenzyloxy)-benzoyl chloride (m.p. 95°) was prepared from the corresponding acid, and reduced to 3,4-(dibenzyloxy)-benzaldehyde (m.p. 86°) by Rosenmund's method. The over-all yield of this aldehyde was 52%, based on the barium carbonate used for preparation of the acid. The aldehyde was debenzylated by hydrogen bromide in acetic acid, and the protocatechualdehyde thus obtained was condensed with malonic acid, to give caffeic acid. Condensation of 3,4-(dibenzyloxy)-benzaldehyde with malonic acid gave 3,4–(dibenzyloxy)-cinnamic acid (m.p. 206–208°) which was converted to dihydrocaffeic acid by catalytic hydrogenation. The over-all yields of caffeic and dihydrocaffeic acids were 36% and 39%, respectively, based on barium carbonate. Protocatechuic acid was readily obtained by hydrogenolysis of 3,4-(dibenzyloxy)-benzoic acid; the yield was 70% based on carbonate.

scholarly journals On the hydrolysis of diethyl 2-(perfluorophenyl)malonate

2020 ◽  
Vol 16 ◽  
pp. 1863-1868
Author(s):  
Ilya V Taydakov ◽  
Mikhail A Kiskin
Keyword(s):  
Acetic Acid ◽  
Malonic Acid ◽  
Diethyl Malonate ◽  
Toxic Substances ◽  
New Approach ◽  
Preparative Yield ◽  
Benzyl Halides ◽  
Acidic Conditions ◽  
Hydrolysis Of ◽  
Sodium Diethyl Malonate

Diethyl 2-(perfluorophenyl)malonate was synthesized in 47% isolated yield by the reaction of sodium diethyl malonate and hexafluorobenzene. The resulting compound was considered as a starting material for synthesizing 2-(perfluorophenyl)malonic acid by hydrolysis. It was found that the desired 2-(perfluorophenyl)malonic acid could not be obtained from this ester by hydrolysis, neither under basic nor under acidic conditions. Nevertheless, hydrolysis of the ester with a mixture of HBr and AcOH gave 2-(perfluorophenyl)acetic acid in a good preparative yield of 63%. A significant advantage of this new approach to 2-(perfluorophenyl)acetic acid is that handling toxic substances such as cyanides and perfluorinated benzyl halides is avoided.

Reaction of13N produced by recoil deuterons in pile-irradiated acetic acid-d4 and malonic acid-d4

1987 ◽  
Vol 118 (1) ◽  
pp. 23-31 ◽  
Author(s):  
Y. Sensui ◽  
K. Tomura ◽  
I. Nakakuki ◽  
H. Suzuki
Keyword(s):  
Acetic Acid ◽  
Malonic Acid

Carbanions in Carbohydrate Chemistry: Synthesis of C-Glycosyl Malonates

1974 ◽  
Vol 52 (8) ◽  
pp. 1266-1279 ◽  
Author(s):  
Stephen Hanessian ◽  
Andre G. Pernet
Keyword(s):  
Acetic Acid ◽  
Malonic Acid ◽  
Diethyl Malonate ◽  
Major Product ◽  
Carbohydrate Chemistry ◽  
Anomeric Configuration ◽  
Bromide Ion ◽  
Chemical Correlation ◽  
Shift Reagents

The condensation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide with sodio diethyl malonate led to crystalline diethyl 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) malonate. The corresponding dibenzyl ester proved to be a versatile intermediate for the preparation of crystalline β-D-glucopyranosyl malonic acid and β-D-glucopyranosyl acetic acid derivatives. The anomeric configuration in these C-glycosides was determined by a chemical correlation. With 2,3,4,6-tetra-O-acetyl- β-D-glucopyranosyl chloride and sodio diethyl malonate, the major product was a 1,2-O-ketal derivative resulting from an attack of the carbanion on the 1,2-acetoxonium ion. The condensation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide with sodio diethyl malonate was conducted with, and without added bromide ion and the mechanistic implications of the results are discussed. C-Glycosides were also prepared in the D-mannofuranose series and their transformation into the D-lyxofuranose series (anomeric mixture) is described. The utility of n.m.r. shift reagents, and an apparent differential complexation by Eu(DPM)3 and Eu(FOD)3-d27 is demonstrated.

scholarly journals Cell Death Triggered by the YUCCA-like Bs3 Protein Coincides with Accumulation of Salicylic Acid and Pipecolic Acid But Not of Indole-3-Acetic Acid

2019 ◽  
Vol 180 (3) ◽  
pp. 1647-1659 ◽  
Author(s):  
Christina Krönauer ◽  
Joachim Kilian ◽  
Tina Strauß ◽  
Mark Stahl ◽  
Thomas Lahaye
Keyword(s):  
Cell Death ◽  
Acetic Acid ◽  
Salicylic Acid ◽  
Pipecolic Acid ◽  
Indole 3 Acetic Acid
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