Repository logo
 

Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin.

Accepted version
Peer-reviewed

Type

Conference Object

Change log

Authors

Schuppe, Alexander W 
Newhouse, Timothy R  ORCID logo  https://orcid.org/0000-0001-8741-7236

Abstract

We report the first total synthesis of the limonoid andirolide N using a 12-step sequence from commercially available materials. The final step of this route demonstrates the chemical feasibility of our biosynthetic proposal that andirolide N arises from 8α-hydroxycarapin. The strategic use of a degraded limonoid as a platform for the synthesis of more structurally complex congeners may be a general approach to obtain limonoids with diverse functional properties.

Description

Keywords

Limonins, Models, Molecular

Journal Title

J Am Chem Soc

Conference Name

ECC23

Journal ISSN

0002-7863
1520-5126

Volume Title

Publisher

American Chemical Society (ACS)
Sponsorship
EPSRC (2458400)
This work was supported by the Engineering and Physical Sciences Research Council and AgriFoRwArdS CDT [EP/S023917/1], by Cambs Farms Growers Limited (G’s Growers), and by the project ‘Agri-station for Automation and Growth Optimization’, within the Observatory for Human-Machine Interaction at the University of Cambridge.