Tandem reversible addition–intramolecular lactonization for the synthesis of 3-functionalized phthalides

Sakulsombat, Morakot; Angelin, Marcus; Ramström, Olof

doi:10.1016/j.tetlet.2009.10.079

Cited by 24 publications

(18 citation statements)

References 25 publications

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“…TBME and THF were tested as enzyme-tolerable solvents besides toluene according to the previous studies. 17,[19][20][21]23,27 The results in TBME were very similar to those obtained in toluene, whereas increased dr and ee from 2 : 1 and 45% to 4.3 : 1 and 65%, respectively, were obtained in THF, indicating that STS favors more polar solvents. Varying the amount of base and enzyme loading did not significantly affect the yield and selectivity.…”

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confidence: 71%

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

Schaufelberger

Zhang

et al. 2013

Chem. Commun.

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supporting

confidence: 71%

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

Schaufelberger

Zhang

et al. 2013

Chem. Commun.

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“…Treatment of (±)- 33 with a controlled source of hydrogen cyanide afforded a cyanophthalide intermediate. 29 Finally, double deprotonation of this intermediate with LiTMP followed by a short exposure to S -phenyl benzenethiosulfonate chemoselectively installed the phenyl sulfide moiety 21 at C6 to provide biaryl (±)- 34 . The observed chemoselectivity in this reaction is a result of the much higher reactivity of the ortho -toluate anion relative to the cyanophthalide anion.…”

Section: Resultsmentioning

confidence: 99%

Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1

2012

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Total syntheses of HMP-Y1, atrop-HMP-Y1, hibarimicinone, atrop-hibarimicinone, and HMP-P1 are described using a two-directional synthesis strategy. A novel benzyl fluoride Michael–Claisen reaction sequence was developed to construct the complete carbon skeleton of HMP-Y1 and atrop-HMP-Y1 via a symmetrical, two-directional, double annulation. Through efforts to convert HMP-Y1 derivatives to hibarimicinone and HMP-P1, a biomimetic mono-oxidation to desymmetrize protected HMP-Y1 was realized. A two-directional unsymmetrical double annulation and biomimetic etherification were developed to construct the polycyclic and highly-oxidized skeleton of hibarimicinone, atrop-hibarimicinone, and HMP-P1. The use of a racemic biaryl precursor allowed for the synthesis of both hibarimicinone atropisomers and provides the first confirmation of the structure of atrop-hibarimicinone. Additionally, this work documents the first reported full characterization of atrop-hibarimicinone, HMP-Y1, atrop-HMP-Y1, and HMP-P1. Lastly, a pH-dependent rotational barrier about the C2–C2' bond of hibarimicinone was discovered, which provides valuable information necessary to achieve syntheses of the glycosylated congeners of hibarimicinone.

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“…The substrates 3‐aryl sulfonylphthalides 1 , [24] 3‐phenyl sulfanylphthalide 4 , [24] 3‐benzotriazolylphthalide 6 , [25] isatylidenemalononitrile 2 , [26] Isatylidenecyanoester 10 , [27] diethyl isatylidenemalonate 11 , [28] and anisaldehyde derived alkylidenemalononitrile 12 [29] were synthesized according to the reported methods.…”

Section: Methodsmentioning

confidence: 99%

“…3‐(Benzylsulfonyl)isobenzofuran‐1(3 H )‐one (1 j) : [24] Methyl 2‐formylbenzoate (1.0 g, 6.1 mmol) was dissolved in CHCl 3 (40 mL). To this solution, triethylamine (8.5 mL, 61 mmol) and benzyl mercaptan (2.9 mL, 24.4 mmol.…”

Section: Methodsmentioning

confidence: 99%

“…The substrates 3-aryl sulfonylphthalides 1, [24] 3-phenyl sulfanylphthalide 4, [24] 3-benzotriazolylphthalide 6, [25] isatylidenemalononitrile 2, [26] Isatylidenecyanoester 10, [27] diethyl isatylidenemalonate 11, [28] and anisaldehyde derived alkylidenemalononitrile 12 [29] were synthesized according to the reported methods. [24] Methyl 2-formylbenzoate (1.0 g, 6.1 mmol) was dissolved in CHCl 3 (40 mL). To this solution, triethylamine (8.5 mL, 61 mmol) and benzyl mercaptan (2.9 mL, 24.4 mmol.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of Sulfonyloxindoles via Functional Group Exchange Between 3‐Sulfonylphthalide and Isatylidenemalononitrile

2021

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An unusual reactivity of 3-sulfonylphthalides with isatylidenemalononitriles has been exploited to provide an efficient entry into 3-sulfonyloxindoles. Although a Hauser-Kraus mechanism can be visualized for the observed transformation, a more probable mechanism, based on control experiments and spectroscopic studies, involves Michael addition of sulfonylphthalide to isatylidenemalononitrile followed by elimination and re-addition of sulfonyl and malononitrile functionalities in an overall functional group exchange between phthalide and oxindolyl moieties. We have also demonstrated the synthetic applications of the sulfonyloxindoles in selected reactions such as conjugate addition and aromatization.

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Tandem reversible addition–intramolecular lactonization for the synthesis of 3-functionalized phthalides

Cited by 24 publications

References 25 publications

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

Efficient asymmetric synthesis of lamivudine via enzymatic dynamic kinetic resolution

Total Syntheses of HMP-Y1, Hibarimicinone, and HMP-P1

Synthesis of Sulfonyloxindoles via Functional Group Exchange Between 3‐Sulfonylphthalide and Isatylidenemalononitrile

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