Total synthesis of (+)-achalensolide based on the Rh(I)-catalyzed allenic Pauson-Khand-type reaction

摘要

[GRAPHICS] The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.