Synthesis of a tetrahydrofuranone prostaglandin analog

Harrison, I. T.; Fletcher, Vernon R.; Fried, Josef

doi:10.1016/s0040-4039(01)91726-5

Cited by 18 publications

(5 citation statements)

References 7 publications

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“…Methyl 4-t-butoxy-2butenoate [2] (1, 11.4 g, 66 mmoles) was added in one portion to the reaction and the mixture stirred 30 minutes in an ice bath and then 1 hour at room temperature. The ether was removed in nacuo and the white solid was dissolved in dimethyl sulfoxide (75 ml).…”

Section: -[(~2-t-butoxyethenyl]-4-hydroxy-2(5h>ranone (3)mentioning

confidence: 99%

“…In this synthesis methyl glycolate alkoxide anion is added in a Michael fashion to the unsaturated ester 1, [2] which then cyclizes to the 4-furanone 2. Isolation, structure proof and possible mechanism of formation are presented J. Heterocyclic Chem., 23, 963 (1986).…”

mentioning

confidence: 99%

“…In this synthesis methyl glycolate alkoxide anion is added in a Michael fashion to the unsaturated ester 1, [2] which then cyclizes to the 4-furanone 2. In this synthesis methyl glycolate alkoxide anion is added in a Michael fashion to the unsaturated ester 1, [2] which then cyclizes to the 4-furanone 2.…”

mentioning

confidence: 99%

“…In connection with our preparation of 2,3-substituted furans as potential thromboxane-A, antagonists we have been using the Gianturco [I] synthesis of furans as applied by Fried and co-workers [2] to prepare starting material 2.…”

mentioning

confidence: 99%

“…In this synthesis methyl glycolate alkoxide anion is added in a Michael fashion to the unsaturated ester 1, [2] which then cyclizes to the 4-furanone 2. During these syntheses, we repeatedly isolated a second major, strongly uv absorbing product 3, which was produced in nearly equal amounts along with the desired 2.…”

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confidence: 99%

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3‐[(Z)‐2‐t‐Butoxyethenyl]‐4‐hydroxy‐2(5H)‐furanone, an interesting byproduct obtained from reaction of 4‐t‐butoxy‐2‐butenoate with the alkoxide anion of methyl glycolate

Arora

Cho

Chadha

et al. 1986

Journal of Heterocyclic Chem

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Treatment of methyl 4‐t‐butoxy‐2‐butenoate (1) with the alkoxide anion of methyl glycolate gives, in addition to the previously reported (Fried, et al. [2]) 2,3‐disubstítuted‐2,3‐dihydro‐4‐furanone 2, an equivalent amount of the interestingly substituted 3‐[(Z)‐2‐t‐butoxyethenyl]‐4‐hydroxy‐2(5H)furanone 3. Isolation, structure proof and possible mechanism of formation are presented

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Section: -[(~2-t-butoxyethenyl]-4-hydroxy-2(5h>ranone (3)mentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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3‐[(Z)‐2‐t‐Butoxyethenyl]‐4‐hydroxy‐2(5H)‐furanone, an interesting byproduct obtained from reaction of 4‐t‐butoxy‐2‐butenoate with the alkoxide anion of methyl glycolate

Arora

Cho

Chadha

et al. 1986

Journal of Heterocyclic Chem

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The Krapcho Dealkoxycarbonylation Reaction of Esters with α‐Electron‐Withdrawing Substituents

Krapcho

Ciganek

2013

Organic Reactions

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The Krapcho reaction involves esters with α‐electron‐withdrawing substituents such as malonates, β‐keto esters, and α‐cyano esters, which undergo dealkoxycarbonylation on being heated in polar aprotic solvents (such as DMSO, DMF, or HMPT) in the presence of water, or in polar aprotic solvents with water in the presence of added salts (such as NaCN, NaCl, LiCl, LiI, or MgCl 2 ). This procedure avoids the use of strongly aqueous acidic and alkaline conditions and tolerates many functional and protecting groups. The chapter presents the mechanistic aspects of this procedure, which include reaction parameters such as solvents, salts, other additives, and the use of microwave irradiation. The diastereoselectivity of protonation of the enolate intermediate leading to the dealkoxycarbonylated products is discussed. Trapping of the intermediate enolate by electrophiles other than a proton is illustrated. Potential side reactions and same‐pot subsequent reactions of substrates are discussed along with functional‐group compatibility for halogens and nitrogen, oxygen, sulfur, selenium, and carbon functional groups. Several examples of applications of this methodology for the synthesis of natural products along with experimental conditions and procedures are presented. Closely related methods are discussed in the Comparison with Other Methods section. The tables, which consist of 371 pages, are grouped according to substrate structure. Selective entries for other methods (excluding classical aqueous acidic or basic methods) are included in the tabular survey for comparative purposes.

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