Organic Letters 2014-02-07

Asymmetric synthesis of (-)-aurantioclavine via palladium-catalyzed intramolecular allylic amination.

Satoshi Suetsugu, Hiromi Nishiguchi, Chihiro Tsukano, Yoshiji Takemoto

Index: Org. Lett. 16(3) , 996-9, (2014)

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Abstract

The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.