Total Synthesis of (?)-Salinosporamide A via a Late Stage C?H Insertion
The synthesis of (?)-salinosporamide A, a proteasome inhibitor, is described. The synthesis highlights the assembly of a densely decorated pyrrolidinone core via an aza-Payne/hydroamination sequence. Central to the success of the synthesis is a late-stage C?H insertion reaction to functionalize a sterically encumbered secondary carbon. The latter functionalization leads to an enabling transformation where most of the prototypical strategies failed.
Gholami, Hadi,Kulshrestha, Aman,Favor, Olivia K.,Staples, Richard J.,Borhan, Babak
p. 10110 - 10113
(2019/04/25)
Formal synthesis of salinosporamide a starting from D-glucose
A formal synthesis of salinosporamide A is described. The tertiary alcohol function in salinosporamide A was stereoselectively generated via the substrate control by the reaction of a cyclic ketone derived from D-glucose with Me3Al, and subsequent Overman rearrangement of an allylic trichloroacetimidate effectively constructed the tetrasubstituted carbon with nitrogen. Formation of g-lactam, followed by the introduction of a cyclohexenyl unit furnished the Corey's intermediate of salinosporamide A. Georg Thieme Verlag Stuttgart.
Entry to heterocycles based on indium-catalyzed Conia-ene reactions: Asymmetric synthesis of (-)-salinosporamide A
Conica can: The In(OTf)3-catalyzed cyclization of nitrogen- and oxygen-tethered acetylenic malonic esters gives five- to seven-membered heterocycles in moderate to excellent yields (see scheme; Tf = trifluoromethanesulfonyl). The asymmetric synthesis of (-)-salinosporamide A illustrates the synthetic utility of the method. (Chemical Equation Presented).
Simple stereocontrolled synthesis of salinosporamide A
A simple and effective stereocontrolled synthesis of salinosporamide A (1) has been developed which follows the pathway outlined in the Figure. The process, the first total synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. In addition to the method of Scheme I, the present invention also includes several novel synthetic intermediate compounds, several intermediate steps of the preferred synthetic process; and the uses of these compounds in the preparation of synthetic derivatives of the compound Salinosporamide A. Salinosporamide A is of special interest as a synthetic target because of its protein in vitro cytotoxic activity against many tumor cell lines (IC50 values of 10 nM or less).
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Page/Page column 10
(2010/02/14)
A simple stereocontrolled synthesis of salinosporamide A
A simple and effective stereocontrolled synthesis of salinosporamide A has been developed. This process, the first synthesis of salinosporamide A, is capable of providing the compound in substantial quantities for further biological studies. Salinosporamide A was of special interest as a synthetic target because of its potent in vitro cytotoxic activity against many tumor cell lines (IC50 values of 10 nM or less). Copyright
Reddy, Leleti Rajender,Saravanan,Corey
p. 6230 - 6231
(2007/10/03)
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