Stereoselective synthesis of the 2,6-disubstituted tetrahydropyran-3-ol of the potent antitumor agent mucocin via an acyl radical cyclization

Evans, P. Andrew; Roseman, Jamie D.

doi:10.1016/s0040-4039(97)01147-7

Cited by 43 publications

(8 citation statements)

References 15 publications

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“…Recently, pyruvic acid (267) was electrochemically synthesized from acetyl chloride (266) and atmospheric CO 2 in an undivided gastight cell with a platinum cathode and a sacrificial zinc anode in DMF containing 0.1 M Bu 4 NBF 4 under a potentiostatic regime (Scheme 199). 359 Since the reaction of an acyl radical with carbon dioxide is extremely inefficient, 360 carboxylation of the acyl anion formed by two consecutive one-electron reductions of acetyl chloride may be reasonably suggested as the key step for this pyruvic acid synthesis.…”

Section: Electrochemical Reduction Of Acyl Radicalsmentioning

confidence: 99%

Chemistry of Acyl Radicals

et al. 1999

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Section: Electrochemical Reduction Of Acyl Radicalsmentioning

confidence: 99%

Chemistry of Acyl Radicals

et al. 1999

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“…In this case the TTCFs become equilibrium time correlation functions. The results for the leading Burnett coefficients are (Evans and Lynden-Bell, 1988):…”

Section: The Inverse Burnett Coefficientsmentioning

confidence: 99%

“…However since until recently no explicit expressions were known for the Burnett coefficients, simulation studies of this possible divergence were severely handicapped. In Chapter 9 we discuss Evans and Lynden-Bell's (1988) derivation of, equilibrium time correlation functions for the inverse Burnett coefficients. The inverse Burnett coefficients are so-called because they refer to the coefficients of the expansion of the forces in terms of the thermodynamic fluxes rather than vice versa.…”

Section: Introductionmentioning

confidence: 99%

Statistical Mechanics of Nonequilbrium Liquids

Morriss¹,

Evans²

2007

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“…[59] Finally,1 ,2-BPSE (7)c an be also used as as urrogate for ethyl radicalc ation, as demonstrated by Evans in his synthesis of the tetrahydropyran core of mucosin (Scheme 38 a). [60] First, 7Z functions as an electrophile and undergoes as ubstitutionr eaction with alcohol 174,e ither by addition-elimination to 7Z or addition to in situ-generated phenylsulfonylacetylene. [61] The vinyl ether in 175 then functions as ar adical acceptori na6exo-trig cyclization with the pendant acyl radical, generating 176 as as ingle diastereomer.N icolaoue tal.…”

Section: Scheme25 To Talsyntheses Of Cristatic Acid (Top)a Nd Ircinimentioning

confidence: 99%

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small‐Molecule Synthons

Trost

Kalnmals

2019

Chemistry A European J

129

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Sulfones are flexible functional groups that can act as nucleophiles, electrophiles, or even radicals. Changing the reaction conditions can completelya lter the reactivity of as ulfonyl group, and as ar esult, molecules bearing multiple sulfones are versatile building blocks. This Review highlights the unique ability of 1,1-and 1,2-bis(sulfones) to masquerade as av ast array of reactive synthons includingm ethane polyanions, vinyl cations,a nd all-carbond ipoles that would be difficultori mpossible to access directly.Scheme1.Selectedsyntheses and reactions of sulfones.Scheme2.Seminaluse of abis(sulfone) as am ethanedianion equivalent.[a] Prof. 11195 MinireviewScheme5.Pd-catalyzed allylic alkylation reactionsw ith bis(sulfones) as methylanion equivalents.Scheme6.Mitsunobumethylationfacilitated by ab is(sulfone) nucleophile.Scheme7.Formal methyl conjugate additiont oa,b-unsaturated aldehydes.Scheme8.Formal methyl conjugate additiont oa na,b-unsaturated ketone.Scheme11. Organocatalytic asymmetric allylic alkylation of Morita-Baylis-Hillmanc arbonates with FBSM.Scheme12. Formal asymmetric fluoromethylationofa ldimines.Scheme13. Formal asymmetric fluoromethylationofa ldehydes.Scheme14. Formal fluoromethylconjugate additionst oenals.Scheme15. Formal fluoromethylconjugate addition to enones.Scheme16. Alkylation of FBSM with alcohols and alkyl halides.Scheme17. Differential reactivity of BDT in difficult alkylation reactions.Scheme18. Annulative Mitsunobu reactionswith bis(sulfone) nucleophiles.Scheme19. Macrocyclizationr eactionsf acilitated by bis(sulfones). Scheme20. Syntheses of insect pheromones facilitated by bis(sulfones).Scheme21. To talsynthesis of (À)-trans-lauthisan.Scheme22. To talsyntheses of constanolactones Aand B.Scheme56. Usingabis(sulfone) to access an ambiphilic carbonyl synthon.Scheme57. Usingabis(sulfone) to access ac arbonyl diradical synthon.Scheme58. Syntheses of (AE)-21-noribogamineand (AE)-ibogamine facilitated by using abis(sulfone) as areplacement for lowmolecular weight olefins.

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Stereoselective synthesis of the 2,6-disubstituted tetrahydropyran-3-ol of the potent antitumor agent mucocin via an acyl radical cyclization

Cited by 43 publications

References 15 publications

Chemistry of Acyl Radicals

Chemistry of Acyl Radicals

Statistical Mechanics of Nonequilbrium Liquids

Sulfones as Chemical Chameleons: Versatile Synthetic Equivalents of Small‐Molecule Synthons

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