3155-55-3

Upstream product

• 117081-50-2 5,6-dihydro-6-ethenyl-4-hydroxy-2H-pyran-2-one 
• 3155-49-5 (E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one 
• 1092383-57-7 4-methoxy-6-vinyl-5,6-dihydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 36281-42-2 1-(4-methoxyphenyl)hex-5-yn-3-ol 

Relevant academic research and scientific papers

Heck-matsuda arylation as a strategy to access kavalactones isolated from polygala sabulosa, piper methysticum, and analogues

Herein, we describe the total syntheses of three bioactive pyrones isolated from Polygala sabulosa (i.e., 1, 4, and 7) and eight isolated from Piper methysticum (i.e., 8-10, 13, 15, and 18-20) using the Heck-Matsuda arylation as the key strategy. The evaluation of this methodology by employing different arenediazonium tetrafluoroborates revealed that the Heck arylation was more efficient when the olefin undergoing arylation possessed the vinyl-2-pyrone structural unit instead of the vinyl dihydro-2-pyrone moiety. The Heck-Matsuda arylation of many of the examined olefins proceeded in a practical manner with total regio- and stereocontrol.

Synthesis of β-methoxyacrylate natural products based on box-Pd IIcatalyzed intermolecular methoxycarbonylation of alkynoles

Bis(oxazoline)-palladium(II) catalyzed carbonylation of homopropargyl alcohols afforded acyclic methoxyacrylate 2 and 6-membered lactone 3a-k in good combined yield. In the case of propargyl alcohols, 5-membered lactones 3p, 3q, 16 were obtained in moderate yields. The one-pot synthesis of kawa lactones 3a, 3r, 3s and formal synthesis of dihydroxycystothiazole A and dihydroxycystothiazole C are presented. To elucidate the stereochemistry of (+)-annularin G and (-)-annularin H, the first asymmetric syntheses of these natural products were achieved.