1999
DOI: 10.1002/(sici)1099-0690(199909)1999:9<2309::aid-ejoc2309>3.0.co;2-9
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Biomimetic Synthesis of the Flavanone Leridol, Revision of the Structure of the Natural Product

Abstract: Two independent syntheses of 5‐hydroxy‐6‐hydroxymethyl‐7‐methoxy‐8‐methylflavanone (1), which was supposed to be natural leridol, demonstrated that this structure assignment was wrong and that the natural flavanone leridol was indeed 5‐hydroxy‐8‐hydroxymethyl‐7‐methoxy‐6‐methylflavanone (2).

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Cited by 29 publications
(13 citation statements)
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“…The filtrate was concentrated in vacuo to give (S)-ethyl 2-methylbutanoate 13 (2.43 g, 64%) as a colorless oil: Rf 0.33 (hexane:EtOAc = 3:1); α ½ 23 D = +18.6 (c 1.15, CHCl 3 ) (lit. [14] α 4.11 | (S)-5-Hydroxy-2,6-dimethyl-3-oxooct-4-enoic acid ethyl ester (14) [17] Ethyl 2-methylacetoacetate 9 (1.22 g, 1.20 mL, 8.20 mmol) was dropwise added to a solution of sodium hydride (0.36 g, 9.00 mmol, 60%) in anhydrous THF (28 mL) at 0 C under nitrogen atmosphere. After 15 min of stirring at 0 C, n-BuLi (5.6 mL, 9.00 mmol, 1.6M) was slowly added.…”
Section: (S)-(+)-ent-phomapyrone Bmentioning
confidence: 99%
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“…The filtrate was concentrated in vacuo to give (S)-ethyl 2-methylbutanoate 13 (2.43 g, 64%) as a colorless oil: Rf 0.33 (hexane:EtOAc = 3:1); α ½ 23 D = +18.6 (c 1.15, CHCl 3 ) (lit. [14] α 4.11 | (S)-5-Hydroxy-2,6-dimethyl-3-oxooct-4-enoic acid ethyl ester (14) [17] Ethyl 2-methylacetoacetate 9 (1.22 g, 1.20 mL, 8.20 mmol) was dropwise added to a solution of sodium hydride (0.36 g, 9.00 mmol, 60%) in anhydrous THF (28 mL) at 0 C under nitrogen atmosphere. After 15 min of stirring at 0 C, n-BuLi (5.6 mL, 9.00 mmol, 1.6M) was slowly added.…”
Section: (S)-(+)-ent-phomapyrone Bmentioning
confidence: 99%
“…Under a nitrogen atmosphere, to a solution of the bispotassium salt 15 (0.39 g, 1.40 mmol) in trifluoroacetic anhydride (7.1 mL), trifluoroacetic acid (0.37 g, 0.24 mL, 3.3 mmol) was dropwise added at -20 C and stirred for 4 h at 0 C. The excess TFA/TFAA was removed under reduced pressure. The remaining traces of TFA could be azeotropically removed with toluene and the crude product was purified by silica gel preparative TLC (MeOH: 4.14 | 4-Hydroxy-3-methyl-6-phenylpyrone (17a) [17][18][19] According to the procedure for the synthesis of the keto ester 14, ethyl benzoate (0.85 g, 0.81 mL, 5.70 mmol) was reacted with the dianion prepared from ethyl 2-methylacetoacetate (1.1 g, 1.1 mL, 7.5 mmol), sodium hydride (0.36 g, 8.2 mmol, 60%), and n-butyllithium (4.7 mL, 7.7 mmol, 1.6M). After work-up followed by chromatography on silica gel (stepwise: 4% EtOAc in hexane to 7% EtOAc in hexane), the keto ester 16 (0.65 mg) was obtained as a yellow oil, which was directly used in the next step.…”
Section: Surugapyrone B (3) [125]mentioning
confidence: 99%
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“…9 The heterocyclic chloromethyl-c-pyrone coupling partner 4 was prepared in four steps from known diketoester 6 (Scheme 2). 10 Monoalkylation of 6 with methyl iodide followed by treating diketoester 7 with DBU and refluxing the mixture in benzene for one hour gave the a-pyrone 8 in acceptable yield. As reported for similar substrates, cyclization of ester 7 to pyrone 8 consistently gave lower yields as the reaction was allowed to reflux for longer reaction times, and when run at reflux in toluene.…”
mentioning
confidence: 96%
“…Almost all the methods of synthesis of flavanones and flavanoids required more amount of heating during the reaction and the yields of the products obtained was less (50-60% yield). [17][18][19] The metabolic fate and toxicity of a molecule is highly dependent upon its structural elements. Exogenous chemicals entering a living system can undergo a number of chemical modifications by a wide array of enzymes, which use these chemicals as substrates.…”
mentioning
confidence: 99%