20901-53-5Relevant academic research and scientific papers
Diastereoselective Cycloaddition of Allyltrialkylsilanes to Intermediate N-Acyliminoesters Obtained from Methyl 4-Methoxy-2-Imidazolidinone- and 2-Oxazolidinone-4-carboxylates
Stahl, Annette,Steckhan, Eberhard,Nieger, Martin
, p. 7371 - 7374 (1994)
The amidoalkylation reaction of methyl 4-methoxy-2-imidazolidinone-4-carboxylates or methyl 4-methoxy-2-oxazolidinone-4-carboxylates using allylsilanes as nucleophiles in the presence of TiCl4 affords three carbon ring annulation products 5 and 9 via a cycloaddition.Besides that, the simple methoxy group substitution product is formed.The ring annulation occurs with practically total diastereoselectivity so that all substituents are located on the β-side of the bicyclic product.
A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
Dransfield, Paul J.,Dilley, Anja S.,Wang, Shaohui,Romo, Daniel
, p. 5223 - 5247 (2007/10/03)
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.
