Total synthesis of zyzzyanones A-D

Academic Article

Abstract

  • Zyzzyanones A-D is a group of biologically active marine alkaloids isolated from Australian marine sponge Zyzzya fuliginosa. They contain a unique bispyrroloquinone ring system as the core structure. The first total synthesis of all four zyzzyanones is described here. The synthesis of these alkaloids started from a previously known 6-benzylamino indole-4,7-quinone derivative and involves 6-7 steps. The key step in the synthesis involves the construction of a pyrrole ring in one step using a Mn(OAc)3 mediated oxidative free radical cyclization reaction of a 6-benzylamino indole-4,7-quinone derivative with 4-benzyloxyphenyl acetaldehyde diethyl acetal in CH3CN. © 2013 Elsevier Ltd. All rights reserved.
  • Digital Object Identifier (doi)

    Author List

  • Nadkarni DH; Murugesan S; Velu SE
  • Start Page

  • 4105
  • End Page

  • 4113
  • Volume

  • 69
  • Issue

  • 20