474499-97-3Relevant academic research and scientific papers
Stereoselective synthesis of (+)-11βH,13-dihydroestafiatin, (+)-11βH,13-dihydroludartin, (-)-compressanolide, and (-)-11βH,13-dihydromicheliolide from santonin
Bargues, Victoria,Blay, Gonzalo,Cardona, Luz,Garcia, Begona,Pedro, Jose R.
, p. 1703 - 1706 (2002)
Starting from 2 and 3, obtained from santonin (1), we have synthesized natural guaianolides 4-7. Chemoselective epoxidation of 2 gave (+)-11βH,13-dihydroestafiatin (4), and epoxidation of 3 followed by regioselective elimination of the hydroxyl group afforded (+)-11βH,13-dihydroludartin (5). Sharpless' mild regioselective ring-opening of 4 and 5 followed by hydrogenolysis yielded (-)-compressanolide (6) and (-)-11βH,13-dihydromicheliolide (7), respectively.
