Synthesis 2016; 48(20): 3429-3448
DOI: 10.1055/s-0035-1562552
review
© Georg Thieme Verlag Stuttgart · New York

Synthetic Approaches to Coronafacic Acid, Coronamic Acid, and Coronatine

Mairi M. Littleson
a  Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow, G1 1XL, UK   Email: allan.watson.100@strath.ac.uk
,
Claire J. Russell
b  Syngenta, International Research Centre, Jealott’s Hill, Bracknell, West Berkshire, RG42 6EY, UK
,
Elizabeth C. Frye
b  Syngenta, International Research Centre, Jealott’s Hill, Bracknell, West Berkshire, RG42 6EY, UK
,
Kenneth B. Ling
b  Syngenta, International Research Centre, Jealott’s Hill, Bracknell, West Berkshire, RG42 6EY, UK
,
Craig Jamieson
a  Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow, G1 1XL, UK   Email: allan.watson.100@strath.ac.uk
,
Allan J. B. Watson*
a  Department of Pure and Applied Chemistry, WestCHEM, University of Strathclyde, Thomas Graham Building, 295 Cathedral Street, Glasgow, G1 1XL, UK   Email: allan.watson.100@strath.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 21 April 2016

Accepted after revision: 25 May 2016

Publication Date:
15 August 2016 (online)


Abstract

The phytotoxin coronatine (COR) is a functional mimic of the active plant hormone (+)-7-iso-jasmonoyl-l-isoleucine (JA-IIe), which regulates stress responses. Structurally, COR is composed of a core unit, coronafacic acid (CFA), which is connected to coronamic acid (CMA), via an amide linkage. COR has been found to induce a range of biological activity in plants and based on its biological profile, COR, as well as CFA, and CMA are attractive starting points for agrochemical discovery, resulting in numerous total synthesis efforts. This review will discuss the synthetic approaches towards CFA, CMA and, ultimately COR, to date.

1 Introduction

2 Total Synthesis of Coronafacic Acid (CFA, 4)

2.1 Mapping Synthetic Strategies

2.2 Intermolecular Diels–Alder Approaches

2.3 Intramolecular Diels–Alder Approaches

2.4 Conjugate Addition Approaches

2.5 Haller–Bauer Approaches

2.6 Intramolecular Cyclisation Approaches

2.7 Oxy-Cope Approaches

3 Total Synthesis of Coronamic Acid (CMA, 5)

3.1 Mapping Synthetic Strategies

3.2 Final Installation of C1

3.3 Final Installation of C2

3.4 Final Installation of C3

4 Total Synthesis of Coronatine (COR, 1)

5 Conclusions

 
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