- Asymmetric synthesis of stigmatellin and crocacin C
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The crystalline sulfone 18 (X-ray analysis), prepared from the monoacetate product [i.e., (+)-12; 98.2% ee] of the lipase PS-catalyzed acetylation of anti,anti-2,4-dimethyl-1,3,5-pentantriol (19a), has been elaborated either to crocacin C (10) or stigmatellin (1), thereby providing a convenient divergent access to these two natural antibiotics.
- Infante-Rodriguez, Carolina,Domon, Lisianne,Breuilles, Pascal,Uguen, Daniel
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- A convenient preparation of elements of the stereotriade
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Enzyme-catalysed acetylation of either syn,syn- or anti,anti-2,4-dimethyl-1,3,5-pentane triol, easily obtained from a mixture of diastereomeric 3-hydroxy-2,4-dimethylglutaric acids, proceeds stereoselectively with preferential attack of the hydromethyl group linked to the R carbon atom of the starting triol, hence providing synthons useful for preparing compounds of the polypropionic pool.
- Domon,Vogeleisen,Uguen
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p. 2773 - 2776
(2007/10/03)
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