METHOD FOR THE PREPARATION OF (±)- CALANOLIDE A AND INTERMEDIATES THEREOF

摘要

A METHOD OF PREPARING (±) -CALANOLIDE A, 1, A POTENT HIV REVERSE TRANSCRIPTASE INHIBITOR, FROM CHROMENE 4 IS PROVIDED. USEFUL INTERMEDIATES FOR PREPARING (±) -CALANOLIDE A AND ITS DERIVATIVES ARE ALSO PROVIDED. ACCORDING TO THE DISCLOSED METHOD, CHROMENE 4 INTERMEDIATE WAS REACTED WITH ACETALDEHYDE DIETHYL ACETAL OR PARALDEHYDE IN THE PRESENCE OF AN ACID CATALYST WITH HEATING, OR A TWO-STEP REACTION INCLUDING AN ALDOL REACTION WITH ACETALDEHYDE AND CYCLIZATION EITHER UNDER ACIDIC CONDITIONS OR MITSUNOBU CONDITIONS, TO PRODUCE CHROMANONE 7. REDUCTION OF CHROMANONE 7 WITH SODIUM BOROHYDRIDE, IN THE PRESENCE OF CERIUM TRICHLORIDE, PRODUCED (±) -CALANOLIDE A. A METHOD FOR RESOLVING (±) -CALANOLIDE A INTO ITS OPTICALLY ACTIVE FORMS BY A CHIRAL HPLC SYSTEM OR BY ENZYMATIC ACYLATION AND HYDROLYSIS IS ALSO DISCLOSED. FINALLY, A METHOD FOR TREATING OR PREVENTING VIRAL INFECTIONS USING (±) -CALANOLIDE OR (-) -CALANOLIDE IS PROVIDED.