Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement

Naoto Hama; Tomoki Matsuda; Takaaki Sato; Noritaka Chida

doi:10.1021/ol900799e

Total synthesis of (-)-agelastatin A: the application of a sequential sigmatropic rearrangement

Org Lett. 2009 Jun 18;11(12):2687-90. doi: 10.1021/ol900799e.

Authors

Naoto Hama¹, Tomoki Matsuda, Takaaki Sato, Noritaka Chida

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

PMID: 19449885
DOI: 10.1021/ol900799e

Abstract

An enantioselective total synthesis of (-)-agelastatin A from (-)-2,3-O-isopropylidene-d-threitol is described. The sequential Overman/Mislow-Evans rearrangement of the allylic bistrichloroimidate is the key step, which efficiently installed a diaminohydroxy group.