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Stereocontrolled synthesis of pseudo C2-symmetric 1,3-diamino-2-propanol core units of HIV protease inhibitors

✍ Scribed by Alessandro Dondoni; Daniela Perrone

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 228 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(96)02355-6

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✦ Synopsis

The synthesis of the pseudo C2-symmetric dibenzyldiamino alcohol (S,S)-I and the two meso stereoisomers la and lb (R = PhCH2) is described by stereocontrolled benzylmagnesium chloride addition to the nitrones 3 derived from chiral ~-amino-c~-hydroxy aldehydes 2 that in turn were obtained from phenylalanine; the overall yield of (S,S)-I is 23% from N-Boc L-phenylalaninal; the antipode (R,R)-1 can be prepared in a similar way starting from the D-isomer of the same c~-amino aldehyde.

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