ChemInform Abstract: Inter‐ and Intramolecular Hetero‐Diels‐Alder Reactions. Part 24. Synthesis of Strictosidine Analogues by Hetero‐Diels‐Alder Reaction and Their Biomimetic Transformation to Indole Alkaloids.

Abstract

Tandem Knoevenagel/hetero‐Diels‐Alder reaction of the aldehyde (I) ‐ derived from tryptamine and a mixed malondialdehyde acetal in a 4‐step procedure ‐ with the barbituric acid (II) and the butenyl ether (III) yields a mixture of the strictosidine analogues (IV) and (VII).