A practical and efficient route to heteraphanes: synthesis of structurally simplified analogues of ansamycins

Abstract

A highly efficient and versatile synthetic strategy has been developed for the synthesis of meta-, para-azabenzeno or azanaphthaleno phanes (II–IV) with varying ring sizes (12–25) through intramolecular Mitsunobu reaction from the corresponding Ns-arylamino alcohols. The reaction is compatible with olefin and ketone moieties in the backbone tether and has been applied in the synthesis of various simplified structural motifs of ansamycins.