Synthesis of Coronafacic Acid via TBAF-Assisted Elimination of the Mesylate and Its Conversion to the Isoleucine Conjugate

2011 ◽  
Vol 13 (16) ◽  
pp. 4232-4235 ◽  
Author(s):  
Yusuke Kosaki ◽  
Narihito Ogawa ◽  
Qian Wang ◽  
Yuichi Kobayashi
Keyword(s):  
Coronafacic Acid

Similarities of the biological activities of coronatine and coronafacic acid to those of jasmonic acid

1996 ◽  
Vol 41 (1) ◽  
pp. 93-96 ◽  
Author(s):  
Yasunori Koda ◽  
Kiyoshi Takahashi ◽  
Yosio Kikuta ◽  
Friedemann Greulich ◽  
Hiroaki Toshima ◽  
...  
Keyword(s):  
Jasmonic Acid ◽  
Biological Activities ◽  
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).

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

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

Investigations of the biosynthesis of the phytotoxin coronatine

1994 ◽  
Vol 72 (1) ◽  
pp. 86-99 ◽  
Author(s):  
Ronald J. Parry ◽  
Sunil V. Mhaskar ◽  
Ming-Teh Lin ◽  
Alan E. Walker ◽  
Robson Mafoti
Keyword(s):  
Amino Acid ◽  
Pseudomonas Syringae ◽  
Cyclopropane Ring ◽  
Carbonyl Oxygen ◽  
Oxidative Cyclization ◽  
Amide Bond ◽  
Hydrogen Atoms ◽  
Coronafacic Acid ◽  
Polyketide Chain ◽  
Oxygen Atoms

The biosynthesis of the phytotoxin coronatine has been investigated by administration of isotopically labeled precursors to Pseudomonas syringae pv. glycinea. The structure of coronatine contains two moieties of distinct biosynthetic origin, a bicyclic, hydrindanone carboxylic acid (coronafacic acid) and a cyclopropyl α-amino acid (coronamic acid). Investigations of coronafacic acid biosynthesis have shown that this compound is a polyketide derived from three acetate units, one butyrate unit, and one pyruvate unit. The two carbonyl oxygen atoms of coronafacic acid were found to be derived from the oxygen atoms of acetate. Additional experiments are described that rule out some possible modes for assembly of the polyketide chain. Coronamic acid is shown to be derived from L-isoleucine via the intermediacy of L-alloisoleucine. Examination of the mechanism of the cyclization of L-alloisoleucine to coronamic acid revealed that the formation of the cyclopropane ring takes place with the removal of only two hydrogen atoms from the amino acid, one at C-2 and the other at C-6. The nitrogen atom at C-2 of L-alloisoleucine is shown to be retained. On the basis of these observations, a mechanism is postulated for the cyclization reaction that involves the diversion of an enzymatic hydroxylation reaction into an oxidative cyclization. Finally, a precursor incorporation experiment with deuterium-labeled coronamic acid demonstrated that free coronamic acid can be efficiently incorporated into coronatine. This observation indicates that the cyclization of L-alloisoleucine to coronamic acid can occur before formation of the amide bond between coronafacic acid and coronamic acid.

Synthesis of (±)-coronafacic acid

1977 ◽  
Vol 18 (49) ◽  
pp. 4331-4334 ◽  
Author(s):  
Akitami Ichihara ◽  
Ryoji Kimura ◽  
Koichi Moriyasu ◽  
Sadao Sakamura
Keyword(s):  
Coronafacic Acid

scholarly journals The structure-activity relationships in coronatine analogs and amino compounds derived from (+)-coronafacic acid.

1979 ◽  
Vol 43 (8) ◽  
pp. 1753-1757 ◽  
Author(s):  
Kunio SHIRAISHI ◽  
Keiichi KONOMA ◽  
Hiroji SATO ◽  
Akitami ICHIHARA ◽  
Sadao SAKAMURA ◽  
...  
Keyword(s):  
Structure Activity Relationships ◽  
Coronafacic Acid ◽  
Structure Activity ◽  
Amino Compounds
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