Total synthesis of (±)-androst-4-en-3-one-17-carboxylic acid

1984 ◽  
pp. 721-723 ◽  
Author(s):  
Jih Ru Hwu ◽  
Eric Jan Leopold
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis

Total syntheses and antiproliferative activities of prenostodione and its analogues

2021 ◽  
Author(s):  
Aldahir Ramos Orea ◽  
María Teresa Ramírez-Apan ◽  
Rosa M. Chávez-Santos ◽  
Rodrigo Aguayo-Ortiz ◽  
Clara I Espitia ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Indole Alkaloid ◽  
Total Syntheses ◽  
Antiproliferative Activities

A high-yielding total synthesis of the indole alkaloid prenostodione was completed in 4 steps and 44% overall yield from 1H-indole-3-carboxylic acid. The expedient syntheses of prenostodiones containing distinct substituents at...

ChemInform Abstract: Total Synthesis of the Marine Toxin Polycavernoside A (I) via Selective Macrolactonization of a Trihydroxy Carboxylic Acid.

ChemInform ◽  
2010 ◽  
Vol 32 (52) ◽  
pp. no-no
Author(s):  
James D. White ◽  
Paul R. Blakemore ◽  
Cindy C. Browder ◽  
Jian Hong ◽  
Christopher M. Lincoln ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Marine Toxin ◽  
Polycavernoside A

Synthesis of Optically Active Hydroxyalkyl Cycloheptatrienes: A Key Step in the Total Synthesis of 6,11-Methylene-LXB4

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 45-50
Author(s):  
Udo Nubbemeyer ◽  
Analuisa Nava ◽  
Lukas Trippe ◽  
Andrea Frank ◽  
Lars Andernach ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis ◽  
Structure Elucidation ◽  
Butyl Ester ◽  
Optically Active ◽  
Chiral Hplc ◽  
Reaction Conditions ◽  
Acid Product ◽  
Tert Butyl ◽  
Nabh4 Reduction

AbstractStarting from methyl cycloheptatrienyl-1-carboxylate, 6-acylation was successfully achieved employing glutaryl chloride in the presence of AlCl3 under controlled reaction conditions to furnish keto carboxylic acid product. After protection of this keto carboxylic acid as tert-butyl ester, reagent-controlled enantioselective reductions delivered configuration-defined methyl-6-hydroxylalkyl cycloheptatriene-1-carboxylates with up to 80% ee. Whereas simple NaBH4 reduction of the keto carboxylic acid and subsequent lactonization afforded a methyl-6-tetrahydropyranonyl cycloheptatriene-1-carboxylate. Resolution using chiral HPLC delivered the product enantiomers with up to >99% ee Finally, ECD analyses enabled structure elucidation. The products are used as key intermediates in enantioselective 6,11-methylene-lipoxin B4 syntheses.

Total synthesis of (+)-polyoximic acid - cis-3-ethylidene-L-azetidine-2-carboxylic acid

1993 ◽  
Vol 34 (26) ◽  
pp. 4157-4160 ◽  
Author(s):  
Stephen Hanessian ◽  
Jian-Min Fu ◽  
José-Luis Chiara ◽  
Romano Di Fabio
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis

Total synthesis of (±)-clavam-2-carboxylic acid

1988 ◽  
Vol 29 (13) ◽  
pp. 1609-1612 ◽  
Author(s):  
E. Arribas ◽  
C. Carreiro ◽  
A.M. Valdeolmillos
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis

Nuclear analogs of β-lactam antibiotics. I. Synthesis of O-2-isocephams

1977 ◽  
Vol 55 (3) ◽  
pp. 468-483 ◽  
Author(s):  
Terrence William Doyle ◽  
Bernard Belleau ◽  
Bing-Yu Luh ◽  
Carrado F. Ferrari ◽  
Michael Patrick Cunningham
Keyword(s):  
Schiff Base ◽  
Carboxylic Acid ◽  
Total Synthesis ◽  
Sodium Borohydride ◽  
Boron Trifluoride ◽  
Cycloaddition Reaction ◽  
Phenoxyacetic Acid ◽  
Azido Group ◽  
Borohydride Reduction ◽  
Sodium Borohydride Reduction

The preparation by total synthesis of a saturated cephalosporin analog 7-β-phenoxyacet-amido-3-ethoxy-O-2-isocepham-4-α-carboxylic acid 30, is described. Compound 30 was prepared via cycloaddition of azidoacetyl chloride to the cinnamylidene Schiff base of ethyl 2-amino-3, 3-diethoxypropionate 13b to give the cis-3-azido-4-styryl β-lactam 15b. Ozonolysis of 15b followed by sodium borohydride reduction gave the alcohol 18b. Boron trifluoride treatment of 18b gave ethyl 7-β-azido-3- β-ethoxy-O-2-isocephem-4-carboxylate 27. Reduction of the azido group followed by coupling with phenoxyacetic acid and saponification of the ester gave 30. The mechanism of the cycloaddition reaction and the stereochemical assignments are also discussed.

ChemInform Abstract: Total Synthesis of (.+-.)-Clavam-2-carboxylic Acid (I).

ChemInform ◽  
1988 ◽  
Vol 19 (34) ◽  
Author(s):  
E. ARRIBAS ◽  
C. CARREIRO ◽  
A. M. VALDEOLMILLOS
Keyword(s):  
Carboxylic Acid ◽  
Total Synthesis
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