Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Musellarins represent a rare class of diarylheptanoid natural products with cytotoxic activity. While total synthesis of musellarins A–C has been reported, musellarins D and E with trans -fused-2,6- cis -dihydropyran (DHP) remain synthetically unexplored. An Achmatowicz rearrangement-based synthetic strategy is developed for the collective total synthesis of musellarins A–E, where synthetic musellarins D and E are achieved for the first time and allow us to correct the misassigned configuration of carbon-10b (C 10b ) as a cis -fused-2,6- cis -THP motif. Notably, palladium-catalyzed arylation of Achmatowicz rearrangement products with boronic acids enables access to both 2,6- trans - and 2,6- cis -dihydropyrans (DHPs), corresponding to musellarins A–C and musellarins D–E, respectively.
Source: The Journal of Organic Chemistry
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G3028491691, Development of Aza-Achmatowicz Rearrangement-based Approach for Construction of 2-ABN and Total Synthesis of Akuammiline Alkaloids, Chemical Synthesis of Broad-spectrum Anticancer Withaferin A and Related Withanolides, Total Synthesis of Spirotetronate Polyketide Spirohexenolides A and B
OpenAlex ID: W4416807872