Organic & Biomolecular Chemistry 2013-10-21

The first asymmetric total synthesis of (+)-coriandrone A and B.

Wenjing Wang, Jijun Xue, Tian Tian, Yingdong Jiao, Ying Li

Index: Org. Biomol. Chem. 11(39) , 6686-90, (2013)

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Abstract

The first enantioselective total synthesis of (+)-coriandrone A and B, two bioactive natural products, has been achieved in 10 steps and 11 steps starting from commercially available methyl 2-hydroxy-4-methoxybenzoate. Key reactions include a Claison rearrangement, a Shi-type epoxidation-cyclization sequence and ortho-metallation of t-butylbenzamides with (S)-(-)-propylene oxide reaction.