Asymmetric Synthesis of (−)-Catunaregin, an Angiogenesis Inhibitor from Mangroves
Abstract
We describe here an enantioselective synthesis of (−)-catunaregin ( 1 ), a bioactive agent from Mangrove plants. Our synthesis features an Evans’ asymmetric syn -aldol reaction, cross-metathesis to an enone, substrate controlled 1,4-addition, a one-pot cyclization to construct the O -bridged tetrahydrofuropyran core, and deprotection to furnish (−)-catunaregin ( 1 ). Our synthetic investigations into the synthesis of (−)-epicatunaregin ( 2 ) from a common intermediate resulted in an interesting structural variant, which was fully characterized by X-ray diffraction analysis. The present synthesis provides convenient access to enantiomeric catunaregin natural products and their structural variants.
Fields of Study & Subjects
Traditional and Medicinal Uses of Annonaceae
Synthesis and Biological Activity
Marine Sponges and Natural Products
Publication details
- Journal / source
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Volume
- 91
- Issue
- 18
- Pages
- 6484–6494
- Publication date
- 22 April 2026
- Language
- EN