The chemistry of indoles. XXXII A facile synthetic method for 6-indolecarbaldehyde, 6-indolemethanol, and 6-substituted 1-hydroxyindoles and its application for the synthesis of a natural alkaloid, (E)-6-(3-methylbuta-1,3-dienyl)indole.

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Abstract
Trivalent titanium ion can reduce arylaldehydes, and the reaction is controllable by selecting the pH of the reaction medium. Utilizing this new finding, 6-indolecarbaldehyde and 6-indolemethanol were convenienthy produced by the modified Leimgruber-Batcho method with titanium(III) chloride as the reducing agent. Syntheses of a natural alkaloid, (E)-6-(3-methylbuta-1, 3-dienyl)indole, and some new 6-substituted 1-hydroxyindoles are also reported