896140-76-4

Upstream product

• 345642-41-3 1,3-bis-(benzyl)-4-(benzyloxy-carbonyl)-2,3-dihydro-1H-imidazol-2-one 
• 288-32-4 1H-imidazole 
• 100-39-0 benzyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 896140-75-3 1,3-bis(benzyl)-4-(hydroxymethylene)-1,3-dihydro-imidazol-2-one 

Downstream Products

• 896140-77-5 1,3-bis(benzyl)-4-(ethylpropenoate)-2,3-dihydro-1H-imidazol-2-one 
• 896141-44-9 (5R,5aR,8S,8aS,8bS)-1,3-Dibenzyl-8b-hydroxy-5-hydroxymethyl-7-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione 
• 908597-32-0 [1,3-dibenzyl-8-(2-chloro-1-triisopropylsilanyloxy-ethyl)-2,4,5-trioxo-2,3,4,7,7a,8-hexahydro-1H-furo[3',4':4,5]benzo[1,2-d]imidazol-4a-ylmethyl]-carbamic acid tert-butyl ester 
• 908597-31-9 [1,3-dibenzyl-8-(2-chloro-1-triisopropylsilanyloxy-ethyl)-2,4,5-trioxo-2,3,4,7,7a,8-hexahydro-1H-furo[3',4':4,5]benzo[1,2-d]imidazol-4a-ylmethyl]-carbamic acid tert-butyl ester 
• 908597-47-7 [1,3-dibenzyl-7-(2-chloro-1-triisopropylsilanyloxy-ethyl)-6-hydroxymethyl-2,4-dioxo-2,3,4,5,6,7-hexahydro-1H-benzoimidazol-5-ylmethyl]-carbamic acid tert-butyl ester 
• 908597-30-8 2-(tert-butoxycarbonylamino-methyl)-3-(1,3-dibenzyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-3-oxo-propionic acid 5-chloro-4-triisopropylsilanyloxy-pent-2-enyl ester 
• 908597-33-1 2-(tert-butoxycarbonylamino-methyl)-3-(1,3-dibenzyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-3-oxo-propionic acid 5-chloro-4-triisopropylsilanyloxy-pent-2-enyl ester 

Relevant academic research and scientific papers

Regiocontrol in MnIII-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers

(Chemical Equation Presented) In control: A cyclization reaction of an allylic β-imidazolinonyl-β-ketoester 1 is carried out in a Mn III-promoted radical cascade. The reaction pathway (5-exo/6-endo or 5-exo/5-exo) can be directed to construct the central cyclopentyl and cyclohexenyl core skeletons (2 and 3) of two classes of oroidin dimers with regiocontrol. An oxidative rearrangement can also be used to convert 2 into 3. PG = protecting group.

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.

Enantioselective strategy to the spirocyclic core of Palau'amine and related bisguanidine marine alkaloids.

[structure: see text] An enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of thi