We describe a new seven-stage synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole, which proceeds via thermal cyclization of the 3-(buta-1,3-dienyl)indoles 7ab and 7bb, prepared from the condensation products of indole-2,3-diones 1a, b and the 3-methyl-4-phenylbut-3-en-2-one 2b. This procedure was also used to prepare related 3-methoxy-1-phenylcarbazole derivatives.
Synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole and related derivatives / E.M. Beccalli, A. Marchesini, T. Pilati. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - :5(1994), pp. 579-587.
Synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole and related derivatives
E.M. BeccalliPrimo
;A. MarchesiniSecondo
;
1994
Abstract
We describe a new seven-stage synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole, which proceeds via thermal cyclization of the 3-(buta-1,3-dienyl)indoles 7ab and 7bb, prepared from the condensation products of indole-2,3-diones 1a, b and the 3-methyl-4-phenylbut-3-en-2-one 2b. This procedure was also used to prepare related 3-methoxy-1-phenylcarbazole derivatives.
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