222307-12-2Relevant academic research and scientific papers
Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N- boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones
Drew, Michael G.B.,John Harrison,Mann, John,Tench, Allen J.,Young, Robert J.
, p. 1163 - 1172 (1999)
We describe the photoinduced addition of methanol to 5(S)-5- triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-5- triisopropylsiloxymethyl-4(S)-hydroxymethyl-pyrrolidine-2-one, and conversion of this into a variety of 4(S), 5(S)-pyrrolidine-2-ones. Photo-induced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-(R)-N-boc-amino]ethyl- tetrahydrofuran-2-one via rearrangement of the initial photoadduct.
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.
