Title

A Chemoenzymatic Approach to Total Synthesis of Epoxyquinol A

Abstract

Epoxyquinol A is a heterodimeric epoxyquinoid that has been shown to inhibit angiogenesis. I present a novel iodolactonization-based approach to the total synthesis of this representative epoxyquinoid. The route relies on the dihydroxylation of benzoates using benzoate-1,2-dioxygenase (BZDO) expressed in Ralstonia eutropha B9 whole cells. The obtained (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid provides a chiral building block from which to pursue asymmetric syntheses of epoxyquinoid natural products. In this synthesis, the iodolactonization strategy is explored for the challenging step of stereoselective installation of an epoxide on the hexadiene ring.

Faculty Sponsor

Jon Collins

Tracks

poster

Terms of Use

If you have questions about permitted uses of this content, please contact the ARMINDA administrator

Location

Cordiner Hall

Presentation Type

Poster

Research Funding Source or OCS Program

Perry Summer Research Award

This document is currently not available here.

Share

COinS
 
Apr 11th, 1:00 PM Apr 11th, 2:00 PM

A Chemoenzymatic Approach to Total Synthesis of Epoxyquinol A

Cordiner Hall

Epoxyquinol A is a heterodimeric epoxyquinoid that has been shown to inhibit angiogenesis. I present a novel iodolactonization-based approach to the total synthesis of this representative epoxyquinoid. The route relies on the dihydroxylation of benzoates using benzoate-1,2-dioxygenase (BZDO) expressed in Ralstonia eutropha B9 whole cells. The obtained (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid provides a chiral building block from which to pursue asymmetric syntheses of epoxyquinoid natural products. In this synthesis, the iodolactonization strategy is explored for the challenging step of stereoselective installation of an epoxide on the hexadiene ring.

Rights Statement

Rights Statement

In Copyright. URI: http://rightsstatements.org/vocab/InC/1.0/
This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).