Zur Chemie des Benzolglykols, III. Über Die Synthese von Vier Stereoisomeren 3.4.5.6‐Tetrahydroxy‐Cyclohexenen (Konduriten)

Nakajima, Minoru; Tomida, Ichiro; Takei, Sankichi

doi:10.1002/cber.19570900217

Cited by 24 publications

(5 citation statements)

References 8 publications

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“…[138] Kara co-workers reported the synthesis of a new inositol analogue, bis-homo-inositol (64), bis-homo-conduritol-D ( 65) and bis-homo-conduritol-F (66), from commercially available 1,3,5,7-cyclooctatetraene (63) (Scheme 18) 139] The first successful and non-stereospecific synthesis of conduritol-A (13) was carried out by Nakajima co-workers. [140] Seçen co-workers have developed a new and stereo-specific synthesis for conduritol-F (18) by different approaches (Scheme 19). [141] Hudlicky co-workers succeeded in the six-step synthesis of pinitol (38) (Scheme 20).…”

Section: Synthetic Production Of Cyclitolsmentioning

confidence: 99%

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Biological Properties of Cyclitols and Their Derivatives

Şimşek Kuş

2023

Chemistry & Biodiversity

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Cyclitols are polyhydroxy cycloalkanes, each containing at least three hydroxyls attached to a different ring carbon atom, and its general formula is CnH2n‐x(OH)x or CnH2nOx. The most important cyclitol derivatives are inositols, quersitols, conduritols and pinitols, which form a group of naturally occurring polyhydric alcohols and are widely found in plants. In addition, synthetic production of cyclitols has gained importance in recent years. Cylitols are molecules synthesized in plants as a precaution against salt or water stress. They have important functions in cell functioning as they exhibit important properties such as membrane biogenesis, ion channel physiology, signal transduction, osmoregulation, phosphate storage, cell wall formation and antioxidant activity. The biological activities of these very important molecules, obtained both synthetically and from the extraction of plants, are described in this review.

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Section: Synthetic Production Of Cyclitolsmentioning

confidence: 99%

“…The first successful and non‐stereospecific synthesis of conduritol‐A ( 13 ) was carried out by Nakajima co‐workers [140] . Seçen co‐workers have developed a new and stereo‐specific synthesis for conduritol‐F ( 18 ) by different approaches (Scheme 19).…”

Section: Synthetic Production Of Cyclitolsmentioning

confidence: 99%

Biological Properties of Cyclitols and Their Derivatives

Şimşek Kuş

2023

Chemistry & Biodiversity

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“…the synthesis from non-cyclitols, non-sugars materials, [6][7][8][9][10][11][12][13][14][15][16] 2. the synthesis from cyclitols, 5,15,[17][18][19] 3. the synthesis from sugar precursors20-25)…”

Section: Streptomycinmentioning

confidence: 99%

A new route to the synthesis of cyclitol derivatives.

1978

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“…The synthesis of conduritol C, one of the cyclohex-5-ene-1,2,3,4-tetrol isomers named conduritols by Kübler in 1908 [ 1 ], has been extensively reported, although only conduritol A and F occur in nature. Since the first racemic synthesis of conduritol C from bromo epi -inositol by McCasland and Reeves [ 2 ], several groups have proposed isolated efforts toward this goal [ 3 , 4 , 5 ]. A chemoenzymatic strategy to obtain enantiomerically pure conduritol C from cyclohexadiene- cis -1,2-diols has also been reported [ 6 , 7 , 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

General Method for the Synthesis of (−)-Conduritol C and Analogs from Chiral Cyclohexadienediol Scaffolds

et al. 2018

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An efficient and facile general method for the synthesis of conduritol C analogs, taking advantage of an enantioselective biocatalysis process of monosubstituted benzenes, is described. The absolute stereochemical patterns of the target molecules (−)-conduritol C, (−)-bromo-conduritol C, and (−)-methyl-conduritol C were achieved by means of chemoenzymatic methods. The stereochemistry present at the homochiral cyclohexadiene-cis-1,2-diols derived from the arene biotransformation and the enantioselective ring opening of a non-isolated vinylepoxide derivative permitted the absolute configuration of the carbon bearing the hydroxyl groups at the target molecules to be established. All three conduritols and two intermediates were crystallized, and their structures were confirmed by X-ray diffraction. The three conduritols and intermediates were isostructural. The versatility of our methodology is noteworthy to expand the preparation of conduritol C analogs starting from toluene dioxygenase (TDO) monosubstituted arene substrates.

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Zur Chemie des Benzolglykols, III. Über Die Synthese von Vier Stereoisomeren 3.4.5.6‐Tetrahydroxy‐Cyclohexenen (Konduriten)

Cited by 24 publications

References 8 publications

Biological Properties of Cyclitols and Their Derivatives

Biological Properties of Cyclitols and Their Derivatives

A new route to the synthesis of cyclitol derivatives.

General Method for the Synthesis of (−)-Conduritol C and Analogs from Chiral Cyclohexadienediol Scaffolds

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