A reductive SN 2' 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.
Keywords: BH3 ⋅ THF; SN2’ reaction; Z-alkene; epoxydienoate; synthesis of torrubiellutin analogue.
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