Anthracyclinones, part 4. The use of DBN or DBU in a novel extension of the Marschalk reaction leading to Hydroxyglycitylanthraquinones

Qureshi, Shireen; Shaw, G.; BURGESS, G. E.

doi:10.1039/p19850001557

Cited by 12 publications

(2 citation statements)

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“…Preparation of Glucose Monomer 4. Synthesis of 4 began with 7 , available in one step from commercially available diacetone glucose (Scheme ). Cleavage of the isopropylidene groups with Dowex H + resin in hot water afforded 8 in excellent yield .…”

Section: Resultsmentioning

confidence: 99%

Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

Leigh

Bertozzi

2008

J. Org. Chem.

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Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel α-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

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Section: Resultsmentioning

confidence: 99%

Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

Leigh

Bertozzi

2008

J. Org. Chem.

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“…Based on the values of coupling constants, the conformation of ring A is probably that shown in structure (13) LJ7. 8 The reactions outlined clearly demonstrate that direct nuclear alkylation of 1,4-diaminoanthraquinone is possible by substantial modification of Marschalk conditions. This method offers advantages over previous indirect routes to such compounds based on the unreliable reaction of ammonia (or amines) with 2-alkylquinizarins.…”

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confidence: 92%

Nuclear alkylation of 1,4-diaminoanthraquinone. Synthesis of chiral 6,11-diaminoanthracyclinones related to ametantrone from carbohydrates

Mills¹,

Mincher²,

Shaw³

1988

J. Chem. Soc., Chem. Commun.

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807 1 DP, U. K, 1,4-Diaminoanthraquinone [leuco derivative (411 with aldehydes in the presence of 1,8-diazabicyclo[5.4.O]undec-7-ene in dimethyl formamide afforded (after aerial oxidation) 2-(hydroxyalkyl)-l,4-diaminoanthraquinones in good yields; reaction of (4) with 1,2-U-isopropylidene-3-U-methyl-cx-~-xylopentod~aldo-l,4-furanose (8) gave, stereospecifically, the hydroxyglycityl derivative (9) which was readily transformed into the novel 6,ll -diaminoanthracyclinone (12).

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