Total synthesis of antofine using Fischer carbene complexes

ORGN 17

Alejandro Camacho-Davila, alcamach@nmsu.edu, Department of Chemistry & Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003 and James W. Herndon, jherndon@nmsu.edu, Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003.

The coupling of a electron rich aromatic ring-substituted alkynylbenzaldehydes or the corresponding benzoyl ketones with gamma,delta-unsaturated carbene complexes has been examined.  The reaction pathway is affected by the electron density at the benzene ring.  Electron rich systems afford dihydrophenanthrenes via a p-quinone methide intermediate.  This reaction has been employed as the cornerstone for a total synthesis of the anticancer agent antofine.