Work

Enantioselective Total Synthesis of (+)-Fusicoccadiene via Photocatalytic Polyene Isomerization

Year: 2025

Type: article

Abstract: The fusicoccane diterpenes have amassed interest for their intricate 5-8-5 tricyclic framework and ability to interface with diverse signaling proteins. Herein, we report an enantioselective synthetic platform for the rapid assembly of fusicoccanes where the 5-8-5 motif is prepared via valence bond isomerization of a polyene precursor. A series of regio- and stereoselective modifications to the periphery of this substructure provides entry to diverse fusicoccane congeners. The utility of this strategy is demonstrated with a concise total synthesis of (+)-fusicoccadiene.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c19654

Authors: Vitalii S. Basistyi, Tyler D. Weinhold, Jacqueline A. Pinkerton, James A. Law, James H. Frederich

Institution: Florida State University

Language: English

Topic: Biological Activity of Diterpenoids and Biflavonoids

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G1584774640, G9000081710