Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors

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-...

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Bibliographic Details
Published in:Tetrahedron 1997-03, Vol.53 (13), p.4769-4778
Main Authors: Gurjar, Mukund K., Pal, Shashwati, Rama Rao, A.V., Pariza, Richard J., Chorghade, Mukund S.
Format: Article
Language:English
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00160-9