Divergent Synthesis of Isochroman-4-ols, 1,3-Dihydroisobenzo-furans, and Tetrahydro-2 H -indeno[2,1- b ]furan-2-ones via Epoxidation/Cyclization Strategy of (E)-(2-Stilbenyl/Styrenyl)methanols.

The resulting solution was evaporated under reduced pressure to give the crude product, which was further purified by column chromatography on silica gel (20% EtOAc/hexane) to furnish B 30 b (49.5 mg, 0.19 mmol, 58%) as a white solid; mp 107.4-107.7 °C. The resulting solution was evaporated under reduced pressure to give the crude product B 29 b , which was further purified by column chromatography on silica gel (20% EtOAc/hexane) to furnish B 29 b (10.5 mg, 0.04 mmol, 75%) as a clear sticky oil. Keywords: epoxidation; cyclization; carbocation; fused-ring systems; stereoselectivity EN epoxidation cyclization carbocation fused-ring systems stereoselectivity 2757 2772 16 08/17/23 20230901 NES 230901 Graph Various oxacycles are privileged scaffolds in pharmaceutical industries, cosmetics, natural products, and drug discovery, among others. TOF-HRMS: I m i / I z i [M + Na] SP + sp calcd for C SB 19 sb H SB 20 sb O SB 4 sb Na: 335.1254; found: 335.1247. tert -Butyldimethyl((3-phenyl-1,3-dihydroisobenzofuran-1-yl)methoxy)silane (26b') By following the General Procedure G, and purification by column chromatography on silica gel (20% EtOAc/hexane), the product (24.0 mg, 0.71 mmol, 44%) was obtained as a yellow sticky gum. [Extracted from the article]