Biological and Medicinal Chemistry

Asymmetric Synthesis of Nodulones C & D by Chemoenzymatic Approach gives Insight into their Biosynthesis

Authors

Abstract

The first asymmetric total synthesis of fungal secondary metabolites, (R)-nodulone C (4) and trans-nodulone D (5) has been reported through the chemoenzymatic approach. The strategy utilizes NADPH-dependent naphthol reductases of Magnaporthe grisea for the reduction of putative biosynthetic substrates, synthesized non-enzymatically in multiple steps. A dihydronaphthalenone 32 and cis-nodulone D (30) has also been synthesized chemoenzymatically. The work implies for similar steps during the biosynthesis of nodulones and their analogs with the involvement of tetrahydroxynaphthalene reductase related enzyme(s).

Content

Thumbnail image of MS-nodulone-TM-2021_1.pdf

Supplementary material

Thumbnail image of SI-nodulone-TM-2021.pdf
Supplementary Information
The file contains procedure for enzyme expression and synthesis of substrates along with NMR, mass and CD spectral data.