Synthesis of nortropane alkaloid calystegine B2 from methyl α-d-xylopyranoside.


Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark. Electronic address: [Email]


A new synthetic route for formation of a central cycloheptanone intermediate leading to the nortropane alkaloid calystegine B2 is described. The approach installs the desired ketone functionality directly in a ring-closing metathesis step. The target compound was prepared over 10 steps from commercially available methyl α-d-xylopyranoside.


Chiral pool synthesis,Ring-closing metathesis,Rotamers,