- 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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p. 308 - 326
(2015/03/04)
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- Toward a total synthesis of stigmatellin; Obtention of an advanced fragment from gallic acid
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Treatment by a base, then an acid, of the ester 3, which was prepared by starting from gallic acid 7a, afforded the chromone 6c, whose Swern oxidation, followed by condensation of the resulting aldehyde 6a with the trienyl lithium derivative 13b and methyl iodide, furnished products isomeric with, but not strictly identical to, an authentic sample of O-benzyl stigmatellin 1c. (C) 2000 Elsevier Science Ltd.
- Domon,Uguen
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p. 5501 - 5505
(2007/10/03)
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- Diastereo- and enantioselective total synthesis of stigmatellin A
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Stigmatellin A (1) isolated from the myxobacterium Stigmatella aurantiaca is a powerful inhibitor of electron transport in mitochondria and chloroplasts. The first highly diastereo- and enantioselective total synthesis of this important natural product is
- Enders, Dieter,Geibel, Gunter,Osborne, Simon
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p. 1302 - 1309
(2007/10/03)
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