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Synthetic studies on pseudolaric acid B: Enantioselective synthesis of C4,C10-di-epi-trans-fused [5-7]-bicyclic skeleton

Abstract Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in… Click to show full abstract

Abstract Studies on the synthesis of antifungal and anticancer natural product, pseudolaric acid B, have led to the enantioselective synthesis of di-epi-trans-fused [5–7]-bicyclic core skeleton. The synthesis was achieved in 10 linear steps, which features the Sharpless asymmetric epoxidation, cyanide-opening reaction of epoxide, and intramolecular [5 + 2] cycloaddition reaction as the key transformations. The stereochemistry was determined by the X-ray crystallographic analysis.

Keywords: synthesis; epi trans; pseudolaric acid; fused bicyclic; enantioselective synthesis; trans fused

Journal Title: Chinese Chemical Letters
Year Published: 2020

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