Methyl 4‐Hydroxy‐5‐iodo‐2,3‐dimethoxy‐6‐methylbenzoate: The Aromatic Fragment of Calichemicin γ. Synthesis, X‐Ray Crystallographic Analysis, and Properties

Abstract

The biologically highly active calichemicin γ contains the benzoate 1 — glycosylated on the OH group and linked through the ester group (S instead of O), via sugar moieties, to other unusual organic fragments. Compound 1 has now been synthesized in five steps from 3,4,5-trimethoxytoluene and has proven to be very interesting. It undergoes spontaneous enantiomer resolution upon crystallization and exhibits second harmonic generation activity.