ChemInform Abstract: Tandem Wessely Oxidation and Intramolecular Diels-Alder Reactions. Part 4. Synthesis of (.+-.)-Coronafacic Acid (XI).

ChemInform ◽  
2010 ◽  
Vol 24 (52) ◽  
pp. no-no
Author(s):  
P. YATES ◽  
N. K. BHAMARE ◽  
T. GRANGER ◽  
T. S. MACAS
Keyword(s):  
Diels Alder ◽  
Coronafacic Acid

Total synthesis of d,l-coronafacic acid by an intermolecular Diels–Alder approach

1984 ◽  
Vol 62 (9) ◽  
pp. 1747-1750 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Montse Llinas-Brunet
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Keto Ester ◽  
Coronafacic Acid

An efficient total synthesis of d,l-coronafacic acid (2) has been achieved from 4-cyclopentene-1,3-dione (4). The synthesis involves keto ester 7 as a key intermediate that is conveniently prepared by the Diels–Alder addition of enedione 4 to ethyl 4-ethyl-2,4-pentadienoate (5).

scholarly journals Expedient Stereoselective Synthesis of Coronafacic Acid Through Intramolecular Diels—Alder Cyclization.

ChemInform ◽  
2007 ◽  
Vol 38 (26) ◽  
Author(s):  
Benoit Moreau ◽  
Maryon Ginisty ◽  
Dino Alberico ◽  
Andre B. Charette
Keyword(s):  
Stereoselective Synthesis ◽  
Diels Alder ◽  
Coronafacic Acid

Expedient Stereoselective Synthesis of Coronafacic Acid Through Intramolecular Diels−Alder Cyclization

2007 ◽  
Vol 72 (4) ◽  
pp. 1235-1240 ◽  
Author(s):  
Benoît Moreau ◽  
Maryon Ginisty ◽  
Dino Alberico ◽  
André B. Charette
Keyword(s):  
Stereoselective Synthesis ◽  
Diels Alder ◽  
Coronafacic Acid

Tandem Wessely oxidation and intramolecular Diels–Alder reactions. IV. The synthesis of (±)-coronafacic acid

1993 ◽  
Vol 71 (7) ◽  
pp. 995-1001 ◽  
Author(s):  
Peter Yates ◽  
N.K. Bhamare ◽  
Thierry Granger ◽  
T.S. Macas
Keyword(s):  
Hydrochloric Acid ◽  
Sodium Ethoxide ◽  
Alder Reaction ◽  
Diels Alder ◽  
Lead Tetraacetate ◽  
Oxidative Decarboxylation ◽  
Coronafacic Acid ◽  
Diels Alder Reaction ◽  
Mild Hydrolysis ◽  
Hydrolysis Of

Ethyl E-5-(4-ethyl-2-hydroxyphenyl)-2-pentenoate (7), prepared in four steps from m-ethylphenol (9), was converted via Wessely oxidation with lead tetraacetate followed by intramolecular Diels–Alder reaction in boiling xylene to ethyl 1-acetyloxy-6-ethyl-2,3,3a,4,5,7a-hexahydro-8-oxo-1,5-methano-1H-indene-anti-4-carboxylate (16). Hydrogenation of 16 followed by mild hydrolysis gave ethyl 6-ethyloctahydro-1-hydroxy-8-oxo-1,5-methano-1H-indene-anti-4-car-boxylate (24), which on oxidation with periodate gave 4-(ethoxycarbonyl)-6-ethyloctahydro-1-oxo-1H-indene-5-car-boxylic acid (26). Oxidative decarboxylation of this gave a mixture of ethyl 6-ethyl-2,3,3a,6,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (31) and ethyl 6-ethyl-2,3,3a,4,7,7a-hexahydro-1-oxo-1H-indene-4-carboxylate (32); the latter was converted to the former by ethanolic sodium ethoxide. Hydrolysis of 31 with hot hydrochloric acid gave (±)-coronafacic acid (4).

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