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Reductive SN2’ Reaction of Epoxydienoate with Borane and its Application to the Synthesis and Structural Revision of an Antitumor Active Torrubiellutin Analogue

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Z-Selective SN2’ reaction of epoxydienoates with borane has been developed. Complete asymmetric transfer occurs to afford skipped dienoates with Z-alkene linked to asymmetric centers on both sides in excellent yields within 10 minutes. A product that has multiple functional groups was applied to the synthesis and structural revision of anti-tumor active analogue of torrubiellutin C.


Abstract

A reductive SN2’ reaction of epoxydienoates and epoxyenoates with borane was developed to afford skipped dienoates and unconjugated enoates with trisubstituted Z-alkene linked to asymmetric centers on one side or both sides. This reaction was successfully applied to the alternative synthesis of an antitumor active artificial analogue of torrubiellutin C. A geometric isomer for α,β-unsaturated amide of the artificial analogue was also synthesized. These syntheses clarified the true structure of the antitumor active artificial analogue of torrubiellutin C.

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