Tetrahedron letters

A facile synthesis of 4-(sulfonylmethyl) indoles from 4-oxo-4, 5, 6, 7-tetrahydroindole: Formal total synthesis of 6, 7-secoagroclavine

N Hatanaka, O Ozaki, M Matsumoto

Index: Hatanaka, Naoto; Ozaki, Osamu; Matsumoto, Masakatsu Tetrahedron Letters, 1986 , vol. 27, # 27 p. 3169 - 3172

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Citation Number: 21

Abstract

-Isomer : NMR (CDCl 3 ) δ 1.66 (d, J=1.3 Hz, 3H), 1.82 (d, J=1.4 Hz, 3H), 3.35 (dd, J=15.8 Hz, J=4.7 Hz, 1H), 3.55 (dd, J=15.8 Hz, J=10.4 Hz, 1H), 4.76 (dd, J=10.4 Hz, J=4.5 Hz, 1H), 4.97 (dt, J=10.8 Hz, J=4.6 Hz, 1H), 5.16 (broad d, J=10.3 Hz, 1H), 6.88(dd, J=6.3 Hz, J=0.9 Hz,1H), 6.93 (s, 1H), 7.13 −7.21 (m, 2H) and 8.03 (broad s, 1H) ppm. -Isomer : Mp 148 – 150 ° C (purified by sublimation). NMR (CDCl 3 ) δ 1.77 (d,J=1.3 Hz,3H), 1.83 (d, J=1.3 Hz,3H) ...