189506-60-3

Basic information

• Product Name: (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester
• Synonyms: (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester
• CAS NO: 189506-60-3
• Molecular Weight: 236.311
• Mol File: 189506-60-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester(189506-60-3)
• EPA Substance Registry System: (E)-4-Methylene-2-((S)-3-oxo-cyclopentyl)-hex-2-enoic acid ethyl ester(189506-60-3)

Safety Data

• Hazardous Substances Data: 189506-60-3(Hazardous Substances Data)

Upstream product

• 59995-48-1 (R)-4-acetoxycyclopent-2-en-1-one 

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.