DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES - SYNTHESIS OF THE MERCK HIV-1 PROTEASE INHIBITOR EPOXIDE INTERMEDIATE

Authors
MALIGRES PE UPADHYAY V ROSSEN K CIANCIOSI SJ PURICK RM ENG KK REAMER RA ASKIN D VOLANTE RP REIDER PJ
Citation
Pe. Maligres et al., DIASTEREOSELECTIVE SYN-EPOXIDATION OF 2-ALKYL-4-ENAMIDES TO EPOXYAMIDES - SYNTHESIS OF THE MERCK HIV-1 PROTEASE INHIBITOR EPOXIDE INTERMEDIATE, Tetrahedron letters, 36(13), 1995, pp. 2195-2198
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
13
Year of publication
1995
Pages
2195 - 2198
Database
ISI
SICI code
0040-4039(1995)36:13<2195:DSO2TE>2.0.ZU;2-B
Abstract
Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bic arbonate results in the diastereoselective formation of the correspond ing iodohydrins 3, 16-22 with essentially no iodolactone by-product. T his methodology has been successfully employed for the synthesis of th e epoxide intermediate 4 of the orally active Merck HIV-I protease inh ibitor L-735,524.