Abstract
AbstractFischer indole synthesis with bicyclic ketones yields regioselectively linear annulated tetracyclic products when starting from ketones with a relative trans configuration. On the other hand, starting materials with a relative cis configuration give exclusively angular annulated indole derivatives. The starting materials were prepared in optically active form in three steps by a sequence of asymmetric Michael reaction, aldol condensation, and catalytic hydrogenation. The last step yields a mixture of cis and trans diastereoisomers which can be separated by column chromatography. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
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