STEREODIVERGENT SYNTHESIS OF ALL DIASTEREOMERS OF 4-AMINOHEPTANE-3,5-DIOL FROM (L)-SERINE

The synthesis of the two diasteromeric meso forms of 4-amino-3,5-hepta nediol (3R,4r,5S)-1a and (3S,4s,5R)-1b and the two pseudo C-2-symmetri c enantiomers (3S,5S)-1c and (3R,5R)-ent-1c is described by stereocont rolled ethylmagnesium bromide or diethylzinc addition to diastereomeri c alpha-amino-beta-hydroxy pentanal derivatives 9 and 13. These deriva tives were prepared from (2S)-N,N-dibenzyl-O-TBS-serinal 2, that in tu rn were obtained from (L)-serine. (C) 1998 Elsevier Science Ltd. All r ights reserved.