Abstract
AbstractA stereoselective synthesis of all functionalized C2–C10 fragment 13 of the antitumor marine natural product clavulactone was accomplished, starting from the commercially available 3‐methylglutaric acid anhydride. Desymmetrization of 3‐methylglutaric acid anhydride with (S)‐α‐phenylethanamine was successfully employed as a key step to embed the isolated C8‐methyl group with the correct absolute configuration (99% de). The C3–C4 cis‐double bond was stereospecifically furnished by an RCM (ring‐closing metathesis) approach. Fragment 13 contains all preset functionalities and will be a useful precursor for the convergent total synthesis of clavulactone.
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