SYNTHESIS OF NOVEL C-2-SYMMETRIC AND PSEUDO C-2-SYMMETRIC BASED DIOLS, EPOXIDES AND DIDEOXY DERIVATIVES OF HIV PROTEASE INHIBITORS

摘要

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-[( I,l-dimethyl ethoxy)-carbonyl]amino-l ,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. (C) 1997 Published by Elsevier Science Ltd. [References: 16]