Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits

Carla M Gauss; Akiyuki Hamasaki; Jay P Parrish; Karen S Macmillan; Thomas J Rayl; Inkyu Hwang; Dale L Boger

doi:10.1016/j.tet.2009.02.065

Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits

Tetrahedron. 2009 Aug 15;65(33):6591-6599. doi: 10.1016/j.tet.2009.02.065.

Authors

Carla M Gauss¹, Akiyuki Hamasaki, Jay P Parrish, Karen S Macmillan, Thomas J Rayl, Inkyu Hwang, Dale L Boger

Affiliation

¹ Department of Chemistry and the Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Abstract

Efficient syntheses and a preliminary evaluation of 1,2,11,11a-tetrahydrocyclopropa[c]-naphtho[2,3-e]indole (CNI) and 1,2,11,11a-tetrahydrocyclopropa[c]naphtho[1,2-e]indole (iso-CNI), and their derivatives containing an anthracene and phenanthrene variant of the CC-1065 or duocarmycin alkylation subunit are detailed.

Abstract

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