A facile synthesis of bispyrroloquinone and bispyrroloiminoquinone ring system of marine alkaloids

Srinivasan Murugesan; Dwayaja H Nadkarni; Sadanandan E Velu

doi:10.1016/j.tetlet.2009.04.021

A facile synthesis of bispyrroloquinone and bispyrroloiminoquinone ring system of marine alkaloids

Tetrahedron Lett. 2009 Jun 24;50(25):3074-3076. doi: 10.1016/j.tetlet.2009.04.021.

Authors

Srinivasan Murugesan¹, Dwayaja H Nadkarni¹, Sadanandan E Velu¹

Affiliation

¹ Department of Chemistry, University of Alabama at Birmingham, 901 14 Street South, Birmingham, Alabama 35294, USA.

Abstract

Bispyrroloquinone and bispyrroloiminoquinone are two important polycyclic ring systems present in biologically active marine alkaloids such as Zyzzyanones, tsitsikammamines and wakayin. A facile synthesis of these two ring systems starting from a 6-benzylamino indole-4,7-quinone or 6-benzylamino pyrroloiminoquinone is described here. This chemistry involves the construction of a pyrrole ring in a single step by treatment of the starting reagents with ethyl acetoacetate or phenylbutane-1,3-dione in the presence of ceric ammonium nitrate in MeOH/CH₂Cl₂ solvent.

Grants and funding

UL1 RR025777/RR/NCRR NIH HHS/United States