Work

Development of Sclareol- and Sclareolide-Based Chemoenzymatic Approaches to Ring Intact and Seco Limonoids

Year: 2025

Type: article

Abstract: The limonoids are a family of tetranortriterpenoids that share a steroid-like ring system with a conserved 3’-substituted furan moiety. The family exhibits a high degree of structural diversity arising from extensive oxidations and skeletal rearrange-ments. This account chronicles the evolution of our chemoenzymatic strategy toward various limonoids from two feedstock terpenes, sclareol and sclareolide. An initial route starting from sclareol successfully delivered the limonoid tetracyclic skele-ton but was deemed to lack the versatility to access more oxidized family members. A second-generation strategy that com-menced from sclareolide was conceived to allow convergent access to gedunin, Corey’s protolimonoid, nimbocinol and aza-diradione. Finally, the strategy was further extended to the synthesis of two ring-seco limonoids, methyl angolensate and mexicanolide.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c06404

Authors: Fang Chen, Jian Li, Hans Renata

Institutions: Rice University, Shanghai Jiao Tong University

Language: English

Topic: Phytochemical compounds biological activities

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: National Science Foundation, Division of Chemistry

Awards: G2080142310, G6671297155, CAREER: Chemoenzymatic Total Synthesis of Terpenoids via P450 Catalysis