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Spiroindimicins B-D were isolated in 2012 from Streptomyces sp. SCSIO 03032,1 a deep-sea derived actinomycete collected from the Bay of Bengal. These hexacyclic natural products feature unprecedented [5,5] spirocyclic bisindole scaffolds, and exhibit moderate inhibitory activity and cytotoxicity against a series of cancer cell lines.1 To date there are no reports on the synthesis of any member of this unusual family of natural products. Our synthetic strategy involves a Fischer indolization between phenylhydrazine 1 and ketone 2 to form the pentacycle 3, to which we are currently attempting to append the pyrrole ring and hence complete the syntheses of spiroindimicins B-D.