Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin.
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
Schuppe, Alexander W
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
1520-5126
Volume Title
Publisher
American Chemical Society (ACS)
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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.