Synthesis and Biological Evaluation of Himanimide C and Unnatural Analogues

Abstract

Recently isolated himanimide C (1) can be prepared via a short, flexible, and stereoselective synthesis using a copper-mediated tandem vicinal difunctionalization of dimethyl acetylenedicarboxylate (DMAD, 8) as a key step. The flexibility of the synthesis is exemplified by the preparation of new unnatural himanimide analogues in order to investigate the fungicidal potency of this new family. [structure: see text]

Enantioselective palladaelectro-catalyzed C–H olefinations and allylations for N–C axial chirality

“…Maleimides represent key structural motifs in several natural products and drug candidates. 18 Hence, we next examined the versatility of the N–C atroposelective transformations with maleimides 12 ( Scheme 2 ). We were pleased to find that the robust electrocatalysis was viable for maleimides 12 .…”

Microwave-assisted synthesis and biological evaluation of 3,4-diaryl maleic anhydride/N-substituted maleimide derivatives as combretastatin A-4 analogues

“…16 The amino-substituted 5f was obtained by reduction of the nitro group of 5b using Na 2 S 2 O 4 in acetone/H 2 O (3:1, v/v) at 50 °C. 17 N-Substituted 3,4-diaryl maleimide 6c was synthesized from hydroxylamine hydrochloride and 3,4-diaryl maleic anhydride 5c in pyridine under the conventional conditions 18 and microwave irradiation, respectively (Table 1). Simultaneously, we optimized the reaction conditions in terms of temperature, reaction time and quantity of hydroxylamine hydrochloride.…”

Metal-Catalyzed Cross-Coupling Reactions of Halomaleic Anhydrides and Halomaleimides: Synthesis of Structurally Interesting and Biologically ­Important Natural and Unnatural Products

“…The obtained product 12b from iodoalkene 12a was further utilized in the synthesis of natural product himanimide C (13) via a saponification-cyclization-imide formation sequence (Scheme 7). 10 Viaud-Massuard and co-workers have developed a new method based on Suzuki cross-coupling reactions between various organoboron derivatives and the diiodomaleimides 14 for the synthesis of a broad range of symmetrically and unsymmetrically substituted di-2-furyl-, di-3-furyl-, and di-2-thienylmaleimides 15 with potential antidiabetic properties (Scheme 8). 11 Routier and co-workers described two different methods for the synthesis of oxophenylarcyriaflavins.…”