Synthesis of the left-hand ring of the antitumor antibiotic CC-1065 by an intramolecular carbenoid addition route. Synthesis and reactivity of 4-diazo-4, 7-dihydroindol- …

…, EW Baxter, WJ Pitts, R Ahmed-Schofield…

Index: Sundberg; Baxter; Pitts; Ahmed-Schofield; Nishiguchi Journal of Organic Chemistry, 1988 , vol. 53, # 21 p. 5097 - 5107

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Citation Number: 29

Abstract

The synthesis of 4-diazo-4, 7-dihydroindol-7-ones, which could serve as precursors of the A- ring structure of the antitumor antibiotic CC-1065 by intramolecular carbenoid addition, has been explored. Direct diazo transfer using 7-hydroxy-3-methyl-5-[N-(2-propenyl) acetamido] indole gave a 6-diazo-6, 7-dihydroindol-7-one. Reduction and diazotiazation of 7- [(ethoxycarbonyl) oxy]-3-methyl-4-nitro-5-[N-(2-propenyl) sulfonamido] indole gave 4- ...