Macrocyclisation of macrodiolide with dimethylaluminium methaneselenolate

Dimethylaluminium methaneselenolate (Me₂AlSeMe, 1) acts as an acyl transfer agent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentially creates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of norpyrenophorin, which result in a macrodilactonisation yield of 64 %. Dimethylaluminium methaneselenolate (Me₂AlSeMe, 1) acts as an acyl transferagent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentiallycreates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of nor-pyrenophorine.