91527-01-4Relevant academic research and scientific papers
Total synthesis of (+)-colletodiol from (S,S)-tartrate and (R)-3-hydroxybutanoate
Schnurrenberger, Peter,Hungerbuehler, Ernst,Seebach, Dieter
, p. 733 - 744 (2007/10/02)
The macrodiolide antibiotic (+)-colletodiol (7, Scheme 1) was synthesised.The configuration was thus proven to be (6R,11R,12R,14R). - Key intermediates (Schemes 9 and 10) are the two hydroxy acids 43 and 64, which were prepared from dimethyl (S,S)-tartrate in 20percent overall yield (12 steps) and from (R)-3-hydroxybutanoate in 57percent overall yield (6 steps), respectively.The two hydroxy acids were cyclised to give, after deprotection, the title compound. - Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.
(+)-COLLETODIOL SYNTHESIS FROM (S,S)-TARTARIC ACID AND (R)-HYDROXY-BUTYRIC ACID
Schnurrenberger, Peter,Hungerbuehler, Ernst,Seebach, Dieter
, p. 2209 - 2212 (2007/10/02)
E-(R)-5-Hydroxy-2-hexenoic acid (4) and the acetonide of E-(4R,5R,7R)-trihydroxy-2-octenoic acid (3) are joined to give, after deprotection, (+)-colletodiol (1).The syntheses of the two hydroxy-acids from poly-(R)-3-hydroxy-butenoate (PHB) and (-)-tartaric acid, respectively, are outlined.
