Biomimetic, Multigram, and Enantioselective Total Synthesis of the Microtubule Destabilizing Pterocarpan (6a S ,11a S )-2,3,9-Trimethoxy-6a,11a-dihydro-6 H -benzofuro[3,2- c ]chromene
Abstract
A four-step (three-pot) and biomimetic total synthesis of the title compound (+)- 1, a pterocarpan-type natural product and microtubule destabilizing agent, was achieved using readily available starting materials. The tetramethoxy-substituted isoflavone 17 was prepared (via ketone 16 ) from these and on treatment with AlCl 3 and sodium iodide this underwent regioselective mono-demethylation to give congener 20 . This was subjected to asymmetric transfer hydrogenation (ATH) and then an acidic workup. By such means the title pterocarpan (+)- 1 was obtained in multigram quantities and >99% ee.
Fields of Study & Subjects
Bioactive natural compounds
Traditional and Medicinal Uses of Annonaceae
Natural Compound Pharmacology Studies
Publication details
- Journal / source
- Organic Process Research & Development
- Publisher
- American Chemical Society (ACS)
- Volume
- 30
- Issue
- 2
- Pages
- 440–449
- Publication date
- 16 January 2026
- Language
- EN