Conduritols and related compounds

Balcı, Metin; Sütbeyaz, Yaşar; Seçen, Hasan

doi:10.1016/s0040-4020(01)90509-5

Cited by 178 publications

(64 citation statements)

References 108 publications

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“…5). 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].…”

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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“…For example, conduramine A (ref. 40) ( 11 ) was prepared from the corresponding A2 –benzene cycloadduct 5a through a modified hydrolysis–oxidation sequence that installed an additional 1,4- syn -aminohydroxy functionality. Accordingly, one-pot successive urazole hydrolysis, hydrazine/oxamic acid oxidation 41 and subsequent hetero Diels–Alder reaction delivered the bicyclic product 10 in 83% yield.…”

Section: Resultsmentioning

confidence: 99%

Dearomative dihydroxylation with arenophiles

et al. 2016

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Aromatic hydrocarbons are some of the most elementary feedstock chemicals, produced annually on a million metric ton scale, and are used in the production of polymers, paints, agrochemicals and pharmaceuticals. Dearomatization reactions convert simple, readily available arenes into more complex molecules with broader potential utility, however, despite substantial progress and achievements in this field, there are relatively few methods for the dearomatization of simple arenes that also selectively introduce functionality. Here we describe a new dearomatization process that involves visible-light activation of small heteroatom-containing organic molecules—arenophiles—that results in their para-cycloaddition with a variety of aromatic compounds. The approach uses N–N-arenophiles to enable dearomative dihydroxylation and diaminodihydroxylation of simple arenes. This strategy provides direct and selective access to highly functionalized cyclohexenes and cyclohexadienes and is orthogonal to existing chemical and biological dearomatization processes. Finally, we demonstrate the synthetic utility of this strategy with the concise synthesis of several biologically active compounds and natural products.

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“…The cyclic polyhdroxylated amines, also known as aminocyclitols, possess a wide variety of biological activities [42–45]. In conclusion, we have outlined the synthesis of a new family of aminocyclitols analogues 6 and 7 based on the bicyclo[4.2.0]octane frame work, with stereocontrol during the formation of all the stereogenic centres.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

Kelebekli¹,

Kara²,

Çelik³

2010

Beilstein J. Org. Chem.

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SummaryA new class of aminocyclitol derivatives with the bicyclo[4.2.0]octane skeleton was synthesized starting from cyclooctatetraene. Photooxygenation of trans-7,8-diacetoxy- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-diene afforded the bicyclic endoperoxides. Reduction of the latter with thiourea followed by a Pd(0) catalyzed ionization/cyclization reaction gave the corresponding oxazolidinone derivatives. Oxidation of the double bond with KMnO4 or OsO4 followed by acetylation gave the acetate derivatives, the exact configuration of which was determined by spectroscopic methods. Hydrolysis of the oxazolidinone rings and removal of the acetate groups furnished the desired aminocyclitols.

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Conduritols and related compounds

Cited by 178 publications

References 108 publications

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Oxovanadium(IV) complexes of carbohydrates: A brief overview

Dearomative dihydroxylation with arenophiles

Synthesis of a new class of aminocyclitol analogues with the conduramine D-2 configuration

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