TOTAL SYNTHESES OF MYRIOCIN AND Z-MYRIOCIN, 2 POTENT IMMUNOSUPPRESSANTS, FROM 2-DEOXY-D-GLUCOSE

Authors
YOSHIKAWA M YOKOKAWA Y OKUNO Y MURAKAMI N
Citation
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
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
22
Year of publication
1995
Pages
6209 - 6228
Database
ISI
SICI code
0040-4020(1995)51:22<6209:TSOMAZ>2.0.ZU;2-P
Abstract
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.