A norbornyl route to cyclohexitols: stereoselective synthesis of conduritol-E, allo-inositol, MK 7607 and gabosines

A novel fragmentation sequence within the norbornane system, involving C1–C7 bond scission, provides convenient access to a highly functionalized and versatile cyclohexenoid building block which has been further elaborated to a range of cyclohexitols such as, conduritol E, allo-inositol and gabosine B. Our synthesis of the structure corresponding to gabosine K indicates that the structure of this natural product needs to be revised.