193530-86-8

Basic information

• Product Name: Propanedioic acid, (4-oxo-2-cyclopenten-1-yl)-, 1,1-dimethylethyl 2-propenyl ester, (1R)-
• CAS NO: 193530-86-8
• Molecular Formula: C15H20O5
• Molecular Weight: 280.321
• Mol File: 193530-86-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, (4-oxo-2-cyclopenten-1-yl)-, 1,1-dimethylethyl 2-propenyl ester, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, (4-oxo-2-cyclopenten-1-yl)-, 1,1-dimethylethyl 2-propenyl ester, (1R)-(193530-86-8)
• EPA Substance Registry System: Propanedioic acid, (4-oxo-2-cyclopenten-1-yl)-, 1,1-dimethylethyl 2-propenyl ester, (1R)-(193530-86-8)

Safety Data

• Hazardous Substances Data: 193530-86-8(Hazardous Substances Data)

Upstream product

• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 
• 134209-82-8 tert-butyl allyl malonate 

Downstream Products

• 189506-61-4 coronatine benzyl ester 
• 62251-96-1 (+)-coronatine 
• 62251-98-3 (+)-coronafacic acid 

Relevant articles and documents

Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine, phytotoxins isolated from Pseudomonas Syringae pathovars

Asymmetric total synthesis of (+)-coronafacic acid (2), was accomplished via intramolecular 1, 6-conjugate addition as the key step. The chiral ester (+)-7 was prepared via two approaches: starting from (R)-(+)-4-acetoxy-2- cyclopenten-1-one (12), and using catalytic asymmetric Michael reactions promoted by heterobimetallic BINOL complexes. Coupling between (+)-2 and the protected coronamic acid 8 and subsequent deprotection by hydrogenolysis provided (+)-coronatine (1). This is the first asymmetric total synthesis of(+)-1.