Total Synthesis of (+)-Fusarochromanone

Description:
 

Reference #:  00365.01

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Invention Description:

This invention is the total synthesis of Forsarochromanone (FC-101), a metabolite of the fungus Fusarium equiseti. This substance is a potent inhibitor of angiogenesis, which is the formation of new blood vessels from existing ones. This process plays a key role in several pathological conditions, including cancer, heart disease and arthritis. The route that was employed in the total synthesis of this natural product is convergent. The longest linear pathway is eight steps. Regioslective aromatic nitration of a benzypyranone intermediate is an important part of this synthesis.

The subject invention also includes the synthesis of an iodobenzopyranone intermediate from the substituted acetophenone, as well as the synthesis of a halozincate side-chain component from an amino acid derivative. The invention also includes C-C bond formation of the two main fragments by a transition metal-catalyzed coupling reaction and subsequent deprotection to furnish the synthetic target in enantiomerically pure form.

Advantages and Benefits:

The invention represents the first total synthesis of fusarochromanone, a small-molecule natural product that heretofore has only been isolated from a natural source (fungus). The synthesis provides a route to material that is identical to the natural material, which was isolated from the natural source.

 

Development:

Each intermediate in the synthesis has been made. The inventor/s has NMR and mass spectral evidence for compounds 1-8, and mass spectral evidence for the existence of nine.

Patent Information:
Title App Type Country Serial No. Patent No. File Date Issued Date Expire Date Patent Status
Synthesis of Chromanones Nationalized PCT United States 10/557,065 7,598,403 11/15/2005 10/6/2009 4/13/2023  
For Information, Contact:
Technology Commercialization
University of South Carolina
technology@sc.edu
Inventors:
Brian Salvatore
Ferdinand Solis
Keywords:
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