Total Synthesis of Mycocyclosin and the Herqulines

Abstract

Since the first reports of their isolation, mycocyclosin and the herquline family of natural products have attracted interest from the synthetic community for their uniquely strained macrocyclic architectures. This review describes the attempted and successful total syntheses of these natural products and provides a summary of the strategies developed in the years since their isolation.

Synthesis of Pentacyclic Framework of Herquline A

“…[5] Formidable structures of herquline natural products have rendered them attractive targets for total synthesis. [6] Earlier studies described in Ph.D. dissertations by the Kang, the Johnson, the Trauner, and the Simpkins groups demonstrated difficulties in forging the strained macrocycle with the C3À C3' connectivity. [7][8][9][10] Notable breakthrough in this field was recorded when the Hutton group reported the first total synthesis of structurally relevant (+)-mycocyclosin (4).…”