Total Synthesis of (–)-Ircinol A, (+)-Ircinal A

Key words

(–)-ircinol A - (+)-ircinal A - [2+2] cycloaddition - retro-Mannich reaction - Mannich reaction - Mander's reagent - Dess–Martin oxidation

Significance

In 1998, Winkler and co-workers reported the first total synthesis of (–)-ircinol A and (+)-ircinal A, two manzamine-related alkaloids from the marine sponge Ircinia. Their work also constitutes a formal synthesis of (+)-Manzamines A and D from the latter (J. Org. Chem. 1992, 57, 2480).

Comment

An efficient [2+2] cycloaddition, retro-Mannich fragmentation, and Mannich reaction se-quence gives rapid access to advanced, tetracyclic intermediate H. Further functional group manipula-tions and macrocyclization to form the 13-membered ring yield (–)-ircinol A and (+)-ircinal A.

Publication History

Article published online:
18 October 2022