109784-19-2Relevant 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.
