No abstract

13-Oxyingenol and its derivatives have high levels of anti-HIV activity. A fully substituted tetracyclic skeleton of 13-oxyingenol is constructed by using spiro-cyclization and ring-closing olefin metathesis as key steps.

The enantioselective synthesis of a seven-membered enone compound, the key intermediate of our previous synthesis of the inside-outside framework of 13-oxyingenol in racemic form, was achieved by using asymmetric cyclopropanation and reductive deoxygenation as key steps.