Synthetic studies of the HIV-1 protease inhibitive didemnaketals: precise and stereocontrolled synthesis of the key mother spiroketal

The precise and stereocontrolled synthesis of the C9–C23 portion, the key mother spiroketal of the HIV-1 protease inhibitive didemnaketals from the ascidian Didemnum sp., has been carried out through multisteps starting from (R)-pulegone as the chiral template. This approach involved the distereoselective construction of eight chiral centers by intramolecular chiral inducement and the coupling of two fragments by Julia reaction.

Graphical abstractThe precise and stereocontrolled synthesis of the C9–C23 portion, the key mother spiroketal of didemnaketals starting from (R)-pulegone.Figure optionsDownload full-size imageDownload as PowerPoint slide