M. K. Gurjar, S. Pal, A. Rao
Mar 31, 1997
Citations
0
Influential Citations
17
Citations
Journal
Tetrahedron
Abstract
The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[(1,1-dimethyl ethoxy)-carbonyl]amino-1,6-diphenylhex-3-ene (4a). Similarly (2S,5S,3E)-2,5-bis-[(1,1-dimethylethoxy)-carbonyl]amino-1-phenyl-6-(p-methoxy)phenylhex-3-ene (4b) was also synthesised from the sulfone (10) and L-tyrosine derived aldehyde (21). These novel intermediates (4a and 4b) were subjected to epoxidation, hydrogenation, hydroboration-oxidation and dihydroxylation reactions. These modifications resulted in the synthesis of known and unknown, C2-symmetric and pseudo-C2-symmetric diamino-epoxides, dideoxy derivatives, diols and deoxy diols based HIV protease inhibitors.