5516-85-8Relevant academic research and scientific papers
Enantioselective Synthesis of Pyrroloindolines via Noncovalent Stabilization of Indole Radical Cations and Applications to the Synthesis of Alkaloid Natural Products
Gentry, Emily C.,Rono, Lydia J.,Hale, Martina E.,Matsuura, Rei,Knowles, Robert R.
supporting information, p. 3394 - 3402 (2018/03/13)
While interest in the synthetic chemistry of radical cations continues to grow, controlling enantioselectivity in the reactions of these intermediates remains a challenge. Based on recent insights into the oxidation of tryptophan in enzymatic systems, we
Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids
Lathrop, Stephen P.,Movassaghi, Mohammad
, p. 333 - 340 (2014/01/06)
We describe the first application of our methodology for heterodimerization via diazene fragmentation towards the total synthesis of (-)-calycanthidine, meso-chimonanthine, and (+)-desmethyl-meso-chimonanthine. Our syntheses of these alkaloids feature an improved route to C3a-aminocyclotryptamines, an enhanced method for sulfamide synthesis and oxidation, in addition to a late-stage diversification leading to the first enantioselective total synthesis of (+)-desmethyl-meso-chimonanthine and its unambiguous stereochemical assignment. This versatile strategy for directed assembly of heterodimeric cyclotryptamine alkaloids has broad implications for the controlled synthesis of higher order derivatives with related substructures.
Enantioselective synthesis of (-)-idiospermuline
Overman, Larry E.,Peterson, Emily A.
, p. 6905 - 6919 (2007/10/03)
The enantioselective total synthesis of the nonacyclic polypyrrolidinoindoline (-)-idiospermuline is described. Stereocontrolled formation of the vicinal quaternary carbon centers is achieved in a single step by dialkylation of an unsymmetrical prostereog
Enantioselective total synthesis of the cyclotryptamine alkaloid idiospermuline
Overman, Larry E.,Peterson, Emily A.
, p. 2525 - 2528 (2007/10/03)
Stereogenic quaternary carbons present the primary challenge in the syntheses of trispyrrolidinoindoline alkaloids such as idiospermuline. In its synthesis the two contiguous quaternary centers are expediently addressed by combining the lithium dienolate
