1029317-06-3Relevant academic research and scientific papers
Synthesis of functionalized pyroglutamic acids, part 1: The synthetic utility of N-acylindole and the ugi reaction with a chiral levulinic acid
Buller, Matthew J.,Gilley, Cynthia B.,Nguyen, Brian,Olshansky, Lisa,Fraga, Breena,Kobayashi, Yoshihisa
scheme or table, p. 2244 - 2248 (2009/04/10)
A variety of pyroglutamic acid derivatives are readily synthesized via N-acylindole intermediates obtained by the Ugi reaction. For the preparation of functionalized pyroglutamic acid derivatives, the diastereoselectivity of the Ugi 4-center 3-component c
2-Nitrophenyl isocyanide as a versatile convertible isocyanide: Rapid access to a fused γ-lactam β-lactone bicycle
Gilley, Cynthia B.,Kobayashi, Yoshihisa
, p. 4198 - 4204 (2008/09/20)
(Chemical Equation Presented) 2-Nitrophenyl isocyanide is introduced as a convertible isocyanide with demonstration of its feasibility and applicability in an efficient synthesis of the fused γ-lactam β-lactone bicycle of proteasome inhibitor omuralide. Starting from a linear keto acid precursor, the fused γ-lactam β-lactone bicycle was prepared in four steps by a sequential biscyclization strategy; a stereocontrolled Ugi reaction and the concomitant direct β-lactonization following the formation of an N-acylbenzotriazole intermediate. The N-acylbenzotriazole is amenable to intra- or intermolecular attack from a variety of nucleophiles with a catalytic amount of base to form the pyroglutamic acid derivatives.
