Synthetic studies of the HIV-1 protease inhibitive didemnaketals: stereocontrolled synthesis of an ester side chain

The stereocontrolled synthesis of the C1–C8 portion, the ester side chain of the HIV-1 protease inhibitive didemnaketals from the ascidian Didemnum sp., has been carried out through 15 steps starting from (S)-carvone as the chiral template. This approach involved the diastereoselective construction of three conjoint chiral centers by intramolecular chiral inducement, and generation of allylic alcohol intermediate through a key Grob fragmentation reaction.