10133-06-9Relevant articles and documents
Novel functionalized acylphosphonates as phosphonoformate analogs
Glabe, Alan R.,Sturgeon, Katherine L.,Ghizzoni, Sally B.,Musker, W. Kenneth,Takahashi, Joyce N.
, p. 7212 - 7216 (1996)
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James et al.
, p. 1806,1809 (1976)
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New total synthesis of (±)-, (-)- and (+)-chuangxinmycins
Kato, Keisuke,Ono, Machiko,Akita, Hiroyuki
, p. 10055 - 10062 (2007/10/03)
(±)-2-Hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 was stereoselectively converted into the (±)-(2,3)-syn-2-thioacetoxy ester 13 with retention of C2-stereochemistry in (±)-6. Palladium-catalyzed cyclization of indolyl iodide and the internal C2 thiol group of the substrate (±)-14 gave the (±)-cis methyl ester 2 of natural chuangxinmycin (1). Stereoselective total syntheses of (-)-(4S,5R)- and (+)-(4R,5S)-chuangxinmycins 1 were achieved based on the enzymatic syntheses of (2R,3S)- and (2S,3R)-epoxy butanoates 9, respectively. Chiral intermediates such as (2R,3S)- and (2S,3R)-2-hydroxy-3-(1H-4′-iodoindol-3′-yl)butanoate 6 for the chiral synthesis of (-)- and (+)-1 were also obtained by the enantioselective hydrolysis of the corresponding acetate (±)-16 by lipase.
Synthesis and Reactions of 3-Hydroxy-2-nosyloxy Esters Produced by the Stereoselective Reduction of 2-Nosyloxy-3-keto Esters
Hoffman, Robert V.,Kim, Hwa-Ok
, p. 6759 - 6764 (2007/10/02)
The reduction of 2-nosyloxy-3-keto esters is an effective method for the preparation of 3-hydroxy-2-nosyloxy esters.The reduction is stereoselective for the syn isomer.The anti isomer can be produced as the major product by the addition of p-nitrobenzenesulfonyl peroxide to ketene bis-silyl acetal derivatives of 3-hydroxy esters.The diastereomers are separable chromatographically and can be converted stereospecifically to glycidic esters and 2-azido-3-hydroxy esters.As such they appear to have excellent potential as versatile synthetic intermediates for the synthesis of 1,2,3-trifunctional substances.
