896141-06-3

Upstream product

• 852615-09-9 (5R,5aS,8S,8aS)-3-(3,4-Dimethoxy-benzyl)-5-hydroxymethyl-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione 
• 3282-30-2 pivaloyl chloride 
• 896141-51-8 (S)-1-(Toluene-4-sulfonyl)-5-triisopropylsilanyloxymethyl-pyrrolidin-2-one 
• 13154-24-0 triisopropylsilyl chloride 
• 17342-08-4 (S)-Pyroglutaminol 
• 4931-66-2 methyl (S)-pyroglutamate 
• 222307-13-3 (S)-(+)-5-(triisopropylsilyloxymethyl)-pyrrolidin-2-one 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 896141-08-5 2,2-dimethyl-propionic acid 3-(3,4-dimethoxy-benzyl)-8b-hydroxy-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,5,5a,6,7,8,8a,8b-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester 

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.