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Paper | Special issue | Vol 99, No. 2, 2019, pp.1217-1225
Published online, 22nd January, 2019
DOI: 10.3987/COM-18-S(F)96
A De Novo Asymmetric Synthesis of Phomopsolide E: A Practical Conversion from Phomopsolide D

Joel M. Harris, Miaosheng Li, and George A. O'Doherty*

*Department of Chemistry and Chemical Biology, Northeastern University, Boston, MA 02115, USA.

Abstract

A practical three-step synthesis of phomopsolide E has been developed from a synthetic sample of phomopsolide D in three steps at 62% yield. A de novo asymmetric synthesis of phomopsolide D was accomplished in 8 steps from an achiral dienone in 47% yield. The initial asymmetry of phomopsolide E was installed by a Sharpless asymmetric dihydroxylation, whereas, a highly diastereoselective reagent control iterative asymmetric hydrogenation reaction was used to diastereoselectively install the pyranone stereochemistry. The net synthetic effort of phomopsolide E was accomplished in a total 11 steps in 40% overall yield. The route as devised provided for the first-time access to synthetic material for biological analysis and established both the absolute and relative stereochemistry for this natural product.