ChemInform Abstract: C(2)-Functionalized Tryptophans from 3-Acetoxyindoles and Their Possible Implication in Indole Alkaloid Biosynthesis.

ChemInform Abstract

The 3-acetoxyindoles (I) react with the nitrosoolefin, generated in situ from the oxime (II), and Na₂CO₃ to give the cycloadducts (III), which are treated with the thiols (IV) to produce the indole derivatives (V). Reduction of (V) leads to the formation of substituted tryptophans. In the case of (V) (R1: -H, R2: -Et), a thio-Claisen rearrangement, yielding (VIII), together with (IX) and (X), is performed. This pathway is assumed to be a part of indole alkaloid biosynthesis.