Organic Letters 2011-02-18

Total synthesis of broussonetine F: the orthoamide Overman rearrangement of an allylic diol.

Naoto Hama, Toshihiro Aoki, Shohei Miwa, Miki Yamazaki, Takaaki Sato, Noritaka Chida

Index: Org. Lett. 13(4) , 616-9, (2011)

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Abstract

A first total synthesis of broussonetine F from diethyl L-tartrate was achieved. The cornerstone of our synthesis was an orthoamide Overman rearrangement, which provided an allylic amino alcohol with complete diastereoselectivity.