Synthesis of mitomycin C analogs. 2. Introduction of a leaving group at C-1 and oxidation of the aromatic ring in 2, 3, 9, 9a-tetrahydro-1H-pyrrolo [1, 2-a] indoles

W Verboom, BHM Lammerink…

Index: Verboom; Lammerink; Egberink; et al. Journal of Organic Chemistry, 1985 , vol. 50, # 20 p. 3797 - 3806

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Citation Number: 21

Abstract

2-(2, 5-Dihydro-lH-pyrrol-l-yl)-a-(phenylmethylene) benzeneacetonitriles 6a, b cyclize thermally in aprotic solvents to the cis-and/or truns-9, 9a-dihydro-3H-pyrrolo [1, 2-a] indoles 7a, 8a and 7b, 8b, respectively. Reaction in methanol affords the 2-(1H-pyrrol-1-y1) benzeneacetonitriles 9a, b as the main products. The appropriate double bond in 8a, b reacts with osmium tetraoxide to give exclusively the cis-vicinal diols 15 and 13, ...