Issue 39, 2013

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

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.

Graphical abstract: The first asymmetric total synthesis of (+)-coriandrone A and B

Supplementary files

Article information

Article type
Communication
Submitted
20 Jul 2013
Accepted
01 Aug 2013
First published
02 Aug 2013

Org. Biomol. Chem., 2013,11, 6686-6690

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

W. Wang, J. Xue, T. Tian, Y. Jiao and Y. Li, Org. Biomol. Chem., 2013, 11, 6686 DOI: 10.1039/C3OB41497C

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