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Studies on Ketoses, 2. Spirocyclic Dihydropyranones from D-Fructose by Frieder W. Lichtenthaler; Walter Doleschal; Susanne Hahn is a Chemistry article available to read on EtoBox.

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Expedient reaction sequences have been developed to convert o-fructose into a diverse collection of spirocyclic dihydropyrandiols with 2S,3S (10, ll), 2R,5S (17, 18), and 2S,3R configuration (19), and of dihydropyranones 4 -7 with 2 s and 2R chirality. Due to the rigid attachment of pyranoid and dioxolane rings around a chiral spiro carbon which is to result in foreseeable regioand stereo-selectivities on additions to the olefinic and/or carbonyl double bonds, they represent highly versatile six-carbon synthons. -Key intermediates for their obtention are the long-known 3-O-benzoyl( 8) and 3-0-tosyl derivatives (12) of 1,2-0-isopropylidene-~-fructopyranose, as well as the novel 4,5-di-Omesyl (9), the 3,4-di-O-tosyl (15), and the 3,4-di-O-benzoyl analogs 23. Introduction of olefinic unsaturation was effected with iodidelzinc in refluxing DMF (Tipson-Cohen procedure) or with triphenylphosphane/iodine/imidazole reagents, carbonyl groups were generated ilia PCC oxidation of the respective alcohols.

Who reads Studies on Ketoses, 2. Spirocyclic Dihydropyranones from D-Fructose?

Author

Frieder W. Lichtenthaler; Walter Doleschal; Susanne Hahn

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); VCH Verlagsgesellschaft; Wiley (ISSN 0947-3440)

Published

1985

Language

EN

Field

Chemistry (Physical Sciences)