CHEMICAL SIMULATION OF TROPIC ACID BIOSYNTHESIS. STEREOSELECTIVE CHEMICAL CONVERSION OF OPTICALLY ACTIVE PHENYLALANINE TO (R)- AND (S)-TROPIC ACID

1976 ◽  
Vol 5 (9) ◽  
pp. 927-932 ◽  
Author(s):  
Shun-ichi Yamada ◽  
Kenji Koga ◽  
Tzuoh Miin Juang ◽  
Kazuo Achiwa
Keyword(s):  
Chemical Conversion ◽  
Optically Active ◽  
Acid Biosynthesis ◽  
Tropic Acid ◽  
Chemical Simulation

ChemInform Abstract: TERREIN, AN OPTICALLY ACTIVE PROSTAGLANDIN SYNTHON OF FUNGAL ORIGIN. I. CHEMICAL CONVERSION TO A COREY-TYPE LACTONE

1978 ◽  
Vol 9 (25) ◽  
Author(s):  
L. A. MITSCHER ◽  
G. W. III CLARK ◽  
G. BOKELMAN ◽  
H. D. H. SHOWALTER ◽  
K. SHIRAHATA ◽  
...  
Keyword(s):  
Chemical Conversion ◽  
Optically Active

Terrein, an Optically Active Prostaglandin Synthon of Fungal Origin. I. Chemical Conversion to a Corey-type Lactone

Heterocycles ◽  
1977 ◽  
Vol 7 (2) ◽  
pp. 779 ◽  
Author(s):  
Lester A. Mitscher ◽  
George W. Clark. III ◽  
Gordon Bokelman ◽  
Hollis D. H. Showalter ◽  
Kunikatsu Shirahata ◽  
...  
Keyword(s):  
Chemical Conversion ◽  
Optically Active

Tropic acid biosynthesis: the incorporation of (RS)-phenyl[2-18O,2-2H]lactate into littorine and hyoscyamine in Datura stramonium

1998 ◽  
pp. 1045-1046 ◽  
Author(s):  
Chi W. Wong ◽  
David O’Hagan ◽  
Chi W. Wong ◽  
John T. G. Hamilton ◽  
David O’Hagan ◽  
...  
Keyword(s):  
Datura Stramonium ◽  
Acid Biosynthesis ◽  
Tropic Acid

Chemical Synthesis of α-Formylphenylacetic Acid, the Postulated Precursor of Tropic Acid

1981 ◽  
Vol 36 (7-8) ◽  
pp. 611-614 ◽  
Author(s):  
Georg G. Gross ◽  
Karl J. Koelen ◽  
Angelika Müller ◽  
Günter Schmidtberg
Keyword(s):  
Chemical Synthesis ◽  
Silica Gel ◽  
Aqueous Media ◽  
Organic Solution ◽  
Acid Biosynthesis ◽  
Tropic Acid ◽  
Ph Values ◽  
Biosynthetic Studies

Abstract a-Formylphenylacetic Acid, Phenylmalonic Semialdehyde, Tropic Acid Biosynthesis a-Formylphenylacetic acid, the postulated immediate precursor of tropic acid, has been synthesized by deacetalization of a-diethoxymethylphenylacetic acid in the presence of silica gel. The compound was reasonably stable in organic solution. In aqueous media, however, a pronounced lability of this semialdehyde was observed at various pH-values (t/2 = 4.5 min at pH 7.4). It is thus very unlikely that this compound can be employed successfully in biosynthetic studies.

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