Metal‐Free trans‐Aziridination of Zerumbone: Synthesis and Biological Evaluation of Aziridine Derivatives of Zerumbone

Abstract

Herein, we describe a metal‐free, iodosobenzene diacetate mediated trans‐aziridination of zerumbone by the direct use of sulfonamides. Preliminary in vitro screening showed that the synthesized compounds had better antiproliferative and antidiabetic activities than the parent compound zerumbone.

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

“…A sulfonyl aziridine group of zerumbone 25 revealed proximity to dienone in X-ray crystal structure. [71] An initial attempt for transannular cyclization with Sc(OTf) 3 under initial optimized conditions with aziridine 25 derived from zerumbone and benzene sulphonamide did not proceed as expected, however, by using catalytic In(OTf) 3 a new [5.8.3] fused-ring system 26 was formed (Scheme 11). [69] To demonstrate the substrate scope, different aziridinated zerumbone derivatives afforded the expected [5.8.3] fused-ring systems in moderate to good yields.…”

“…Aziridination or epoxidation of the isolated double bond confer conformational alterations in zerumbone that has implications in Lewis acid‐catalyzed transannular cyclization reactions. A sulfonyl aziridine group of zerumbone 25 revealed proximity to dienone in X‐ray crystal structure [71] . An initial attempt for transannular cyclization with Sc(OTf) 3 under initial optimized conditions with aziridine 25 derived from zerumbone and benzene sulphonamide did not proceed as expected, however, by using catalytic In(OTf) 3 a new [5.8.3] fused‐ring system 26 was formed (Scheme 11).…”