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

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.

SUBMITTER: Murugesan S

PROVIDER: S-EPMC4331033 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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

Murugesan Srinivasan S Nadkarni Dwayaja H DH Velu Sadanandan E SE

Tetrahedron letters 20090601 25

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 ...[more]

PMID: 25698845

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