M. Yoshikawa et al., TOTAL SYNTHESES OF MYRIOCIN AND Z-MYRIOCIN, 2 POTENT IMMUNOSUPPRESSANTS, FROM 2-DEOXY-D-GLUCOSE, Tetrahedron, 51(22), 1995, pp. 6209-6228
Total syntheses of myriocin (thermozymocidin, ISP-1, 21) and its analo
g, Z-myriocin (22), which showed potent immunosuppressive activity, we
re accomplished starting from 2-deoxy-D-glucose by employing a modifie
d Darzen reaction as a key reaction. The stereoselectivity of the modi
fied Darzen reaction for six-membered cyclic ketones was discussed on
the basis of physicochemical evidence including the conformational ana
lyses of the cyclic ketones based on molecular mechanics calculation.