Concise Asymmetric Total Synthesis of ent-Guadinomic Acid from an Epoxy Alkenol

Abstract

A highly efficient asymmetric total synthesis of ent-guadinomic acid [(-)-K01-0509 B] was accomplished from the known epoxy alkenol which is resolved by HKR method. Cross metathesis of the alkene part with acrylate and epoxide opening with azide followed by intramolecular guanidine formation reactions furnished ent-guadinomic acid.

Key words

cyclic guanidine - epoxides - guadinomic acid - meta­thesis - total synthesis

References and Notes

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15

The reason for the improvement of the regioselectivity is not clear.

17

The bulky and less nucleophilic Hünig’s base might minimize side reactions associated with the highly reactive Tf₂O.