73344-10-2

Upstream product

• 62251-98-3 (+)-coronafacic acid 
• 18598-74-8 methyl L-isoleucinate hydrochloride 
• 190073-22-4 (3aS,6R,7aS)-ethyl 6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-carboxylate 
• 115074-49-2 (1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 
• 73-32-5 L-isoleucine 
• 1315607-61-4 diethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 
• 1315607-66-9 (S,E)-ethyl 4-(((methylsulfonyl)oxy)methyl)-2-((S)-3-oxocyclopentyl)hex-2-enoate 
• 1315607-65-8 (S,E)-ethyl 2-((1S,3R)-3-hydroxycyclopentyl)-4-(((methylsulfonyl)oxy)methyl)hex-2-enoate 
• 1315607-64-7 (S,E)-ethyl 2-((1S,3R)-3-((tert-butyldimethylsilyl)oxy)cyclopentyl)-4-(((methylsulfonyl)oxy)methyl)hex-2-enoate 
• 1315607-59-0 C₂₂H₄₄O₉S₂Si 
• 1315607-63-6 (4R)-ethyl 2-((1S,3R)-3-((tert-butyldimethylsilyl)oxy)cyclopentyl)-3-hydroxy-4-(hydroxymethyl)hexanoate 
• 1315607-67-0 C₂₆H₅₄O₅Si₂ 
• 1315607-62-5 C₂₆H₅₂O₅Si₂ 

Relevant academic research and scientific papers

Dual function of coronatine as a bacterial virulence factor against plants: Possible COI1-JAZ-independent role

Coronatine (COR, 1) is a phytotoxin and structural mimic of the plant hormone (+)-7-iso-jasmonoyl-L-isoleucine (2). COR (1) functions as a ligand of the COI1-JAZ co-receptor, which is the exclusive receptor of 2. Recently, a new role for 1 as a plant viru

Synthesis of coronafacic acid via TBAF-assisted elimination of the mesylate and its conversion to the isoleucine conjugate

An aldol reaction followed by elimination of the derived mesylate was used to construct the side chain that was designed to afford the cyclohexene ring of coronafacic acid via intramolecular alkylation. Elimination of the mesylate proceeded with TBAF. The