Bioinspired Total Synthesis and Structure-Activity Relationship Studies on Aplaminal

The total synthesis of aplaminal having a unique triazabicyclo[3.2.1]octane skeleton was accomplished using biomimetic oxidative cyclization as a key reaction. This total synthesis enabled us to prepare aplaminal analogs with a variety of substituents at the para-position in the aromatic ring. We found that an electron-donating group at the para-position enhances cytotoxicity and a hydrogen bond donor at the para-position is suitable for cytotoxicity.

Automated summary

The total synthesis of aplaminal with a unique skeleton was achieved, and the effects of different substituents at the para-position on cytotoxicity were investigated.