New and convenient synthesis of (R)-(+)-4,5-Dihydro-4-methyl-2(3H)-furanone and (R)-(-)-4-Bromo-3-methyl-1-O-tert-butyldimethyl-silylbutan-1-ol

Stereoselective Synthesis of the C1–C9 and C11–C25 Fragments of Amphidinolides C, C2, C3, and F

“…Lactone 9 was then prepared from 8 via acidic bis-deketalization and spontaneous lactonization, followed by substrate-controlled diastereoselective hydrogenation and selective silylation of the primary alcohol. Lactone 9 was further converted into acrylate 10 in a three-step sequence that involved protection of the diols as MOM acetals using P 2 O 5 and CH 2 (OCH 3 ) 2 in chloroform, DIBAL-H reduction, and Wittig olefination (Scheme ). Next, 10 was treated with TBAF to induce a diastereoselective intramolecular hetero-Michael cyclization to form the trans -2,5-disubstituted tetrahydrofuran ring with desilylation to reveal the C9 primary alcohol.…”