896141-39-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 98-79-3 L-Pyroglutamic acid 
• 222307-13-3 (S)-(+)-5-(triisopropylsilyloxymethyl)-pyrrolidin-2-one 
• 4931-66-2 methyl (S)-pyroglutamate 
• 17342-08-4 (S)-Pyroglutaminol 
• 13154-24-0 triisopropylsilyl chloride 
• 896141-34-7 3-(4-methoxybenzyl)-1-toluenesulfonyl-4-(ethylpropenoate)-2,3-dihydro-1H-imidazol-2-one 
• 896141-32-5 3-(4-methoxybenzyl)-1-(toluene-4-sulfonyl)-4-(hydroxymethyl)-1,3-dihydro-imidazol-2-one 
• 896141-29-0 1-(p-toluenesulfonyl)-3-(4-methoxybenzyl)-4-(methoxycarbonyl)-2,3-dihydro-1H-imidazol-2-one 
• 896141-51-8 (S)-1-(Toluene-4-sulfonyl)-5-triisopropylsilanyloxymethyl-pyrrolidin-2-one 
• 896141-33-6 3-(4-methoxybenzyl)-1-(toluene-4-sulfonyl)-4-formyl-2,3-dihydro-1H-imidazol-2-one 
• 852615-13-5 1-(p-toluenesulfonyl)-4-(methoxycarbonyl)-2,3-dihydro-1H-imidazol-2-one 
• 896141-36-9 3-(4-methoxybenzyl)-1-toluenesulfonyl-4-(3-hydroxypropenyl)-1,3-dihydro-imidazol-2-one 
• 345642-39-9 (S)-1-(Toluene-4-sulfonyl)-5-triisopropylsilanyloxymethyl-1,5-dihydro-pyrrol-2-one 

Downstream Products

• 896140-95-7 (5R,5aS,8S,8aS)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione 
• 896140-99-1 (5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione 

Relevant academic research and scientific papers

A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine.