Synthesis of Novel C2-symmetric and Pseudo C2-symmetric Based Diols, Epoxides and Dideoxy Derivatives of HIV Protease Inhibitors

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, C 2 -symmetric and pseudo-C 2 -symmetric diamino-epoxides, dideoxy derivatives, diols and deoxy diols based HIV protease inhibitors.