Synthesis of (5,6)‐epoxy‐(1α, 2β, 3α, 4β)‐(±)‐5‐cyclohexane‐ 1‐3H, 2,3, 4‐3H ‐tetrol. (3H ‐Conduritol B epoxide)

Gal, Andrew E.; Voorstad, Josée P.

doi:10.1002/jlcr.2580240407

Cited by 12 publications

(4 citation statements)

References 21 publications

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“…Dibromodiol 6 can be obtained from p -benzoquinone in two steps which yield 90% of an isomeric mixture containing 80−90% of the all-trans isomer (Scheme ). Acetylation of 6 and recrystallization from ethanol gives pure diacetate 7 on a multigram scale (68%). Hydrolysis of 7 is described by Johnson with lipase Amano PS-30 in buffer pH 8 at 50 °C (16 h).…”

Section: Resultsmentioning

confidence: 99%

New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (−)-LL-C10037α, and (+)-KT 8110

et al. 2000

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A practical route is decribed for the preparation of the C(7)N core of manumycin-type compounds. Starting from p-benzoquinone, optically pure compounds in both forms can be prepared via enzymatic resolution of a derived diacetoxy conduritol. A diepoxy aminoinositol is accessible which can function for formation of enantiopure epoxyquinones and quinols. Examples are given for acylation reactions of this amine with several acyl derivatives. With this approach (-)-LL-C10037alpha and quinones such as (+)-KT-8110 with 5R,6S-configuration can be synthesized through oxidation. In addition a short route to (+)-bromoxone is described. Most steps include simple epoxide formation and cleavage reactions which all can be carried out in a high stereoselective manner.

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Section: Resultsmentioning

confidence: 99%

New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (−)-LL-C10037α, and (+)-KT 8110

et al. 2000

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“…We report the regio-and stereospecific synthesis of dimethoxy chiro- The title compound was prepared in 87% yield (recrystallized from AcOEt/hexane), as described in the literature. [54][55][56][57] (±)-(1RS,2RS,3SR,6SR)-3,6-Dimethoxycyclohex-4-ene-1,2-diyl diacetate (11) 6-dimethoxycyclohex-4-ene-1,2-diyl diacetate 11 [30] (1.58 g, 89%) as colorless crystals.…”

Section: Enzyme Inhibition Resultsmentioning

confidence: 99%

“…The title compound was prepared in 87% yield (recrystallized from AcOEt/hexane), as described in the literature. [ 54–57 ]…”

Section: Methodsmentioning

confidence: 99%

“…termediate, allylic trans-diol 9, for the synthesis of the target compounds was obtained as the sole product by stereoselective reduction of the carbonyl groups with NaBH 4 in ether. [54][55][56] Dimethoxydiol 10, which is a conduritol-B derivative, was obtained from the reaction of dibromodiol 9 with sodium methoxide prepared by dissolving sodium metal in methanol under nitrogen atmosphere in high yields (87%). [57,58] The stereochemical course of the transformation was mainly determined as the trans configuration to methoxy groups.…”

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confidence: 99%

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Concise syntheses and some biological activities of dl‐2,5‐di‐O‐methyl‐chiro‐inositol, dl‐1,4‐di‐O‐methyl‐scyllo‐inositol, and dl‐1,6‐dibromo‐1,6‐dideoxy‐2,5‐di‐O‐methyl‐chiro‐inositol

Aksu

Akıncıoğlu

Gülçın

et al. 2020

Archiv der Pharmazie

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The regio‐ and stereospecific synthesis of O‐methyl‐chiro‐inositols and O‐methyl‐scyllo‐inositol was achieved, starting from p‐benzoquinone. After preparing dimethoxy conduritol‐B as a key compound, regiospecific bromination of the alkene moiety of dimethoxy conduritol‐B and acid‐catalyzed ring opening of dimethoxydiacetate conduritol‐B epoxide with Ac2O afforded the desired new chiro‐inositol derivatives and scyllo‐inositol derivative, respectively. Spectroscopic methods were employed for the characterization of all synthesized compounds. The novel inositols (11–17) had effective inhibition profiles against human carbonic anhydrase isoenzymes I and II (hCA I and II) and acetylcholinesterase (AChE). The novel inositols 11–17 were found to be effective inhibitors against AChE, hCA I, and hCA II enzymes. Ki values were calculated in the range of 87.59 ± 7.011 to 237.95 ± 17.75 μM for hCA I, 65.08 ± 12.39 to 538.98 ± 61.26 μM for hCA II, and 193.28 ± 43.13 to 765.08 ± 209.77 μM for AChE, respectively. Also, due to the inhibitory effects of the novel inositols 11–17 against the tested enzymes, these novel inositols are potential drug candidates to treat some diseases such as glaucoma, epilepsy, leukemia, and Alzheimer's disease.

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Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

2001

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Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relevant molecule is formed from benzoquinone. A conduritol A derivative is synthesized in eight steps from benzoquinone and is then subjected to the palladium reaction. From this flexible intermediate, four epimers of the aminocyclitol, including the natural one, can be obtained with complete stereoselectivity. Racemic conduritol B derivatives are available in four steps from benzoquinone, and these are then made enantiomerically pure by a palladium-catalyzed dynamic kinetic resolution. From the chiral conduritol B, the aminocyclitol is available in six steps. Excellent levels of enantio- and diastereoselectivity highlight these strategies.

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Synthesis of (5,6)‐epoxy‐(1α, 2β, 3α, 4β)‐(±)‐5‐cyclohexane‐ 1‐³H, 2,3, 4‐³H ‐tetrol. (³H ‐Conduritol B epoxide)

Cited by 12 publications

References 21 publications

New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (−)-LL-C10037α, and (+)-KT 8110

New Stereoselective Route to the Epoxyquinol Core of Manumycin-Type Natural Products. Synthesis of Enantiopure (+)-Bromoxone, (−)-LL-C10037α, and (+)-KT 8110

Concise syntheses and some biological activities of dl‐2,5‐di‐O‐methyl‐chiro‐inositol, dl‐1,4‐di‐O‐methyl‐scyllo‐inositol, and dl‐1,6‐dibromo‐1,6‐dideoxy‐2,5‐di‐O‐methyl‐chiro‐inositol

Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

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