Journal of Organic Chemistry 2012-11-02

Total synthesis of (-)-orthodiffenes A and C.

Jun Liu, Yi Liu, Xing Zhang, Chaoli Zhang, Yangguang Gao, LinLin Wang, Yuguo Du

Index: J. Org. Chem. 77(21) , 9718-23, (2012)

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Abstract

The efficient and concise synthesis of (-)-orthodiffenes A and C has been accomplished for the first time in eight steps from readily available chiral synthons, D-mannose and D-ethyl lactate. Our work confirmed the complete structure of orthodiffenes A and C, including their absolute stereochemistry. The key steps of our total synthesis involved cis-fused tetrahydrofuran cyclization, one-pot deprotection-lactonization, and intramolecular benzoyl migration according to a biosynthetic hypothesis of orthodiffenes.