68421-48-7

Upstream product

• 38236-17-8 isocostus lactone 
• 69075-77-0 gallicin 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 38236-17-8 isocostus lactone 
• 122052-27-1 Toluene-4-sulfonic acid (3S,3aS,6R,6aS,9R,9aS,9bS)-9-hydroxy-3,9-dimethyl-2-oxo-dodecahydro-azuleno[4,5-b]furan-6-yl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of (+)-11βH,13-dihydroestafiatin, (+)-11βH,13-dihydroludartin, (-)-compressanolide, and (-)-11βH,13-dihydromicheliolide from santonin

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.

Biomimetic cyclization of gallicin to form guaianolides1 1 Part 43 in the series Chemistry of the Composites. For Part 42, see: A.G. Gonzalez, A. Galindo, H. Mansilla and A. Alemany, Tetrahedron Letters 376

A biomimetic-type cyclization of gallicineas carried out to form guaianolides. The possible mechanism is discussed and the stereoselectivity of the reaction explained by a preferred reacting conformation.