The rhodium carbenoid route to cyclic ethers: synthesis of the cis-2,7-disubstituted oxepane skeleton of isolaurepinnacin
Abstract
The cis-2,7-disubstituted oxepane skeleton 1 of the marine natural product isolaurepinnacin 2 has been obtained by three routes, all of which involve a rhodium(II) acetate mediated cyclisation of diazo alcohols to give the functionalised oxepanes 3, 4 and 5, suitable for further elaboration into the common intermediate, the oxepan-3-one 8.