- N-heterocyclic carbene-catalyzed benzoin strategy for divergent synthesis of cyclitol derivatives from alditols
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A divergent synthesis of cyclitol derivatives has been developed utilizing an N-heterocyclic carbene-catalyzed benzoin-type cyclization of C2-symmetrical dialdoses. The resulting inososes are versatile intermediates, which are readily converted
- Kang, Bubwoong,Sutou, Toshiaki,Wang, Yinli,Kuwano, Satoru,Yamaoka, Yousuke,Takasu, Kiyosei,Yamada, Ken-Ichi
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p. 131 - 147
(2015/01/30)
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- Synthesis of allo - And epi -inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes
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A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
- Stockton, Kieran P.,Greatrex, Ben W.,Taylor, Dennis K.
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p. 5088 - 5096
(2014/06/23)
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