合成路线1

Synthesis of fostriecin: The reduction of tetrahydrofuranone (VI) with DIBAL gives the lactol (VII), which is mesylated with Ms-Cl and treated with TEA to yield the dihydrofuran (VIII). The Sharpless asymmetric dihydroxylation of (VIII) with (DHQD)2AQN affords the diol (IX), which is selectively monosilylated with Tbdms-OTf, providing the silyl ether (X). The condensation of the lactol (X) with phosphonate (XI) by means of KHMDS gives the methyl heptenoate (XII). The silylation of the OH group of (XII) with Tes-OTf yields the disilylated ester (XIII), which is reduced with DIBAL to afford the primary alcohol (XIV). The oxidation of (XIV) with DMP provides the corresponding aldehyde (XV), which is treated with CBr4 and PPH3 to furnish the alpha,alpha-dibromodiene (XVI). Elimination of the Pmb-protecting group of (XVI) with DDQ gives the primary alcohol (XVII), which is treated with Ac2O to yield the acetate (XVIII). The selective monodebromination of (XVIII) with Bu3SnH and Pd(PPh3)4 affords the bromoolefin (XIX), which is condensed with tributylstannane (XX) to provide the adduct (XXI). Cleavage of the acetoxy group of (XXI) by means of DIBAL gives the primary alcohol (XXII).