Practical synthesis of ECH and epoxyquinols A and B from (−)-shikimic acid†
Abstract
An efficient synthesis of ECH, epoxyquinols A and B, and two bioactive analogs EqM and RKTS-33 has been completed starting from (−)-shikimic acid. Rapid establishment of the desired epoxyquinol core is facilitated through a key allylic oxidation with high stereoselectivity, which is achieved by fine tuning the cyclohexene substrate structure and reaction conditions.