Total Synthesis of Aspergillomarasmine A and Related Compounds: A Sulfamidate Approach Enables Exploration of Structure–Activity Relationships

• DOI: 10.1002/ange.201606657
• Publication Date: 2016-09-16T09:34:43Z
• Authors: Silvia A. Albu; Kalinka Koteva; Andrew M. King; Salma Al‐Karmi; Gerard D. Wright; Alfredo Capretta
• Keywords: Secondary metabolite; Structure–activity relationship

Abstract The fungal secondary metabolite aspergillomarasmine A (AMA) has recently been identified as an inhibitor of metallo‐β‐lactamases NDM‐1 and VIM‐2. Described herein is efficient practical route to AMA its related compounds by a sulfamidate approach. In addition, series derivatives prepared tested for biological activity in effort explore preliminary structure relationships. While it was determined that natural LLL isomer remains the most effective inactivator enzyme both vitro cells, highly tolerant changes stereochemistry at positions 3, 6, 9.