Stereospecific Photochemical Cyclization of Azidoquinone with E, E-and Z, Z-Dienes. Application to the Synthesis of an Important Precursor toward Mitomycins

Y Naruta, N Nagai, T Yokota, K Maruyama

Index: Naruta, Yoshinori; Nagai, Naoshi; Yokota, Tadafumi; Maruyama, Kazuhiro Chemistry Letters, 1986 , p. 1185 - 1188

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Citation Number: 8

Abstract

Photochemical reaction of 5-azido-2-methoxy-3-methyl-1, 4-benzo quinone with cis, cis-2, 4- hexadien-1, 6-diol derivatives stereoselectively affords the corresponding 2, 3- dihydroindolequinone, which possesses trans configuration at 2, 3-position and vinylic double bond preserves the original stereochemistry of the diene. It is efficiently converted to a key precursor in mitomycin synthesis.