189506-59-0

Usage

Chemical Structure

Ethyl ester of (S)-1,4-dioxaspiro[4.4]nonane-7-acetic acid with a spirocyclic structure

Application

Organic synthesis

Potential Use

Pharmaceutical and medicinal chemistry

Role

Building block for the synthesis of biologically active compounds and pharmaceutical intermediates

Enantiomer Importance

(S)-enantiomer plays a crucial role in determining biological and pharmacological activities

Significance

Valuable component in drug discovery and development

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 academic research and scientific papers

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.

Asymmetric total syntheses of (+)-coronafacic acid and (+)-coronatine

An asymmetric total synthesis of (+)-coronafacic acid, starting from (R)-(+)-4-acetoxy-2-cyclopen-1-one as a chiral source, was accomplished. Construction of the 1-hydrindanone framework was carried out by using intramolecular 1,6-conjugate addition as the key step. Coupling between (+)-coronafacic acid and protected coronamic acid, and subsequent deprotection provided (+)-coronatine. This is the first asymmetric total synthesis of (+)-coronatine.