Tetrahedron p. 1501 - 1508 (1989)
Update date:2022-09-26
Topics:
Cardillo, Giuliana
Orena, Mario
Romero, Marta
Sandri, Sergio
The alkylation of the chiral enolates of glycolate imides 2a and 2b proceedes in highly diastereoselective manner to give 2'-substituted products in good yield.Reductive cleavage with LiBH4 affords the corresponding 2-benzyloxyalcohols 3a-c and 11a-b which are successively converted to 1,2-diols in high optical purity.By this method (R)-1-propanoyloxy-2,3-propanediol 9 and (S)-1-tridecyloxy-2,3-propanediol 14, a glyceride extracted from sponges Plocamiidae, have been synthesized, starting from 2a and 2b, respectively.
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Doi:10.1055/s-0029-1219586
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(2010)
