Winkler JD,
*,
Axten JM.
The University of Pennsylvania, Philadelphia, USA
The First Total Syntheses of Ircinol A, Ircinal A, and Manzamines A and D.
J. Am. Chem. Soc. 1998;
120: 6425-6426
DOI:
10.1021/ja981303k
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.
