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

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

Organic & biomolecular chemistry (2013-08-30)
Wenjing Wang, Jijun Xue, Tian Tian, Yingdong Jiao, Ying Li
초록

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.