Concise Asymmetric Total Syntheses of (+)-Dihydropleurotinic Acid and (-)-Pleurotin, Enabling Rapid Late-Stage Diversification.

ABSTRACT: (-)-Pleurotin (1) and (+)-dihydropleurotinic acid (2) are benzoquinone meroterpenoids isolated from fungal sources with powerful antitumor and antibiotic activities. Concise asymmetric total syntheses of the stereochemically pure (+)-dihydropleurotinic acid (2) and (-)-pleurotin (1) from the chiral pool (R)-Roche ester-derived vinyl bromide 7 have been achieved in 12 and 13 longest linear steps, respectively. The key transformations feature a Michael addition/alkylation cascade reaction to forge three contiguous stereocenters matched with the natural products, a PtO₂-catalyzed stereoselective reduction of olefin to generate the correct stereocenter at C3, a palladium-catalyzed Negishi cross-coupling between triflate and zinc reagent to i

SUBMITTER: Huang B 

PROVIDER: S-EPMC11600149 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature