Aryl Amidation Routes to Dihydropyrrolo[3,2-e]indoles and Pyrrolo[3,2-f]tetrahydroquinolines:  Total Synthesis of the (±)-CC-1065 CPI Subunit

2007-01-19T00:00:00Z (GMT) by Michael D. Ganton Michael A. Kerr
CC-1065 and the related duocarmycins are members of a structurally unique family of naturally occurring molecules and remain some of the most rigorously studied antitumor compounds to date. Herein we describe a total synthesis of the (±)-CC-1065 CPI subunit in an overall yield of 9.3% from commercially available 5-fluoro-2-nitrophenol. The key steps of this synthesis are a Diels−Alder reaction of an o-benzoxy-monoimine quinoid and an intramolecular aryl triflate amidation, which formed the pyrrolo[3,2-f]tetrahydroquinoline intermediate en route to CPI.