Die Biosynthese der Cyclite

Kindl, Helmut; Scholda, R.; Hoffmann‐Ostenhof, O.

doi:10.1002/ange.19660780305

Cited by 12 publications

(3 citation statements)

References 49 publications

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“…The so-called conduritols A and F are naturally occurring products [33][34][35]. Optically active conduritol F is found in small quantities in almost all green plants whereas the occurrence of the meso conduritol A is restricted to specific families of tropical plants [35,36]. The other four isomeric species (B, C, D and E) do not occur naturally.…”

Section: Vo 2+ Complexes Of Conduritols and Related Ligandsmentioning

confidence: 99%

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Baran¹

2009

Journal of Inorganic Biochemistry

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Section: Vo 2+ Complexes Of Conduritols and Related Ligandsmentioning

confidence: 99%

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Baran¹

2009

Journal of Inorganic Biochemistry

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“…Optically active conduritol F is found in small quantities in almost all green plants whereas the occurrence of the meso conduritol A is restricted to specific families of tropical plants [10,11]. The other four isomeric species (B, C, D and E) do not occur naturally.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and biological activity of oxovanadium (IV) complexes with cyclic polyalcohols

Etcheverry¹,

Barrio²,

Zinczuk³

et al. 2005

Journal of Inorganic Biochemistry

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“…[3] Conduritols and their derivatives display some interesting biological activities, which make their chemical synthesis attractive. Conduritol A derivatives, for example, exhibit insulin-modulating activity, [4] while conduritol epoxides and aminoconduritols are potent glycosidase inhibitors and have been shown to inhibit human immunodeficiency virus (HIV).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Both Enantiomers of Conduritol C Tetraacetate and of meso‐Conduritol D Tetraacetate by Oxidation of Benzoquinone Bis(ethylene acetal)

Lang

Ziegler

2007

Eur J Org Chem

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Epoxidation of p‐benzoquinone bis(ethylene acetal) (1) with m‐chloroperbenzoic acid or hydrogen peroxide/benzonitrile afforded corresponding monoepoxide 2, which was converted into p‐benzoquinone mono(ethylene acetal) monoepoxide 5 with perchloric acid. Dihydroxylation of 1 with osmium tetroxide or ruthenium trichloride/sodium periodate afforded corresponding cis‐diol 6, which was subsequently acetylated to give diacetate 7. One ethyleneacetal moiety in 7 could be selectively hydrolyzed with silica gel/ferric chloride under solvent‐free conditions to give ketone 8, which, upon reduction with sodium borohydride and subsequent acetylation of the formed alcohol group, afforded two diastereomeric triacetates 10. Hydrolysis of the remaining acetal functions in the two diastereomers 10, followed by reduction of the second carbonyl group as described above, afforded racemic conduritol C and meso‐conduritol D tetraacetates 12 and 13, respectively. Enzymatic resolution of the racemic arabino‐configured triacetate 10 with Lipozym failed, while the ribo‐configured counterpart reacted smoothly to give enantiomerically pure D‐ribo‐ and L‐ribo‐configured triacetates 10. The latter pair of enantiomerically pure triacetates were converted into both enantiomers of conduritol C tetraacetate 13 as described for the racemic compounds. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Die Biosynthese der Cyclite

Cited by 12 publications

References 49 publications

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Synthesis, characterization and biological activity of oxovanadium (IV) complexes with cyclic polyalcohols

Synthesis of Both Enantiomers of Conduritol C Tetraacetate and of meso‐Conduritol D Tetraacetate by Oxidation of Benzoquinone Bis(ethylene acetal)

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