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Totally Synthetic by Paul H. Docherty, 21 April 2006

Total Synthesis of Agelastatin A


B. M. Trost, G. Dong, J. Am. Chem. Soc. 2006, 128, 6054-6055.

DOI: 10.1021/ja061105q

A very rapid total synthesis of Agelastatin A, using palladium chemistry (no surprise!) in two steps. However, both these steps go in remarkable yield, completing the 5-6-5 core of the target in four steps!

The remaining 5-member ring is constucted in an elegant two-step process; aziridination using a new-to-application N-heterocyclic carbene catalyst, followed by hydrolytic ring opening. A very interesting total synthesis.