A Chiral Pool Approach for Total Synthesis of (+)‐Diaportinol, (−)‐Peniisocoumarin H and (+) & (−)‐Desmethyldiaportinol; Their Structural Revision

Abstract

First stereoselective total synthesis of (+)-diaportinol, (À )-peniisocoumarin H and (+)-& (À )-desmethyldiaportinol is demonstrated and their absolute stereochemistry was revised accordingly. A convergent approach has been developed that uses L-malic acid as chiral synthons for the synthesis of 2, and D-malic acid for 1 and 3. O,O-Dimethylorsellinic acid ester was prepared and coupled with Weinreb amide 6 or 6D via lateral lithiation carbonylation and a subsequent base catalyzed cyclization provided the isochromenone moiety and a selective deprotection was achieved using BBr 3 .