By Irene Hsiao
The Rawal lab has published a total synthesis of the indole alkaloid (−)-ambiguine P, a hapalindole-type natural product isolated from cyanobacteria in 2010. Members of this family of alkaloids demonstrate antifungal and antibacterial properties−some comparable to antibiotics in popular use. Furthermore, their complex pentacyclic structures have proven a fascinating challenge to synthetic organic chemists. In "Total Synthesis of (−)-Ambiguine P," published 11 March 2019 in JACS, Rawal and graduate student Jiasu Xu devised a strategy that enabled the construction of this intricate molecule through a remarkably concise route. Their work lays the foundation for synthesis of other pentacyclic members of the ambiguine alkaloid family.