Asymmetric Total Synthesis of (+)-Chuanxiongnolide L1 via a Stereoselective Oxidative Dearomatization/Diels-Alder Strategy.

ABSTRACT

The first asymmetric total synthesis of chuanxiongnolide L1 was achieved in 16 steps and 1.9% overall yield by employing a bioinspired chiral auxiliary strategy. The key steps involving asymmetric oxidative dearomatization of chiral amino ether and subsequent asymmetric Diels-Alder reaction of the resulting masked chiral ortho-benzoquinone were adopted.