Asymmetric construction of all-carbon quaternary stereocenters by chiral-auxiliary-mediated Claisen rearrangement and total synthesis of (+)-bakuchiol.

Ken-ichi Takao, Shu Sakamoto, Marianne Ayaka Touati, Yusuke Kusakawa, Kin-ichi Tadano

Index: Molecules 17(11) , 13330-44, (2012)

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Abstract

An asymmetric Claisen rearrangement using Oppolzer’s camphorsultam was developed. Under thermal conditions, a geraniol-derived substrate underwent the rearrangement with good stereoselectivity. The absolute configuration of the newly formed all-carbon quaternary stereocenter was confirmed by the total synthesis of (+)-bakuchiol from the rearrangement product.