An efficient total synthesis of the anticancer agent (+)-spisulosine (ES-285) from Garner’s aldehyde

An efficient total synthesis of (+)-spisulosine (ES-285) was completed in nine steps from (S)-Garner’s aldehyde. The vicinal amino alcohol moiety with anti-configuration was achieved by a highly diastereoselective addition of vinyl magnesium bromide to Garner’s aldehyde. The long hydrocarbon chain of the antitumor natural product was installed via olefin cross metathesis of the benzyl-protected allylic alcohol with an appropriate olefin counterpart followed by hydrogenation.