Total Syntheses of Myriocin and Z-Myriocin, Two Potent Immunosuppressants, from 2-Deoxy-D-Glucose

Article abstract of DOI:10.1016/0040-4020(95)00279-H

Total syntheses of myriocin (thermozymocidin, ISP-1, 21) and its analog, Z-myriocin (22), which showed potent immunosuppressive activity, were accomplished starting from 2-deoxy-D-glucose by employing a modified Darzen reaction as a key reaction.The stereoselectivity of the modified Darzen reaction for six-membered cyclic ketones was discussed on the basis of physicochemical evidence including the conformational analyses of the cyclic ketones based on molecular mechanics calculation.