The Journal of organic chemistry

Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties

P Lan, MG Banwell, AC Willis

Index: Lan, Ping; Banwell, Martin G.; Willis, Anthony C. Journal of Organic Chemistry, 2014 , vol. 79, # 7 p. 2829 - 2842

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Citation Number: 10

Abstract

Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1, 2-dihydrocatechol 5 as starting material. Key steps include Suzuki–Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/ rearrangement reactions. As a result of these studies, the structures of ribisins A and D ...