Palladium Catalyzed Synthesis of the Furanoterpene Ircinin-4

Fürstner, Alois; Gastner, Thomas; Rust, Jörg

doi:10.1055/s-1999-2534

Cited by 27 publications

(12 citation statements)

References 10 publications

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“…20 A potentially general route to 2,4-disubstituted furans has been used by Fürstner and his co-workers in a synthesis of the terpene ircinin-4, the structure of which incorporates a 2,4-dialkylfuran subunit. 21 This makes use of essentially the same methodology as was invented for 2,4-disubstituted pyrroles in Fürstner's route to roseophilin and which is outlined in Section 4 (see Scheme 26).…”

Section: Furans and Benzofuransmentioning

confidence: 99%

Synthesis of aromatic heterocycles

Gilchrist¹

1999

J. Chem. Soc., Perkin Trans. 1

200

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Section: Furans and Benzofuransmentioning

confidence: 99%

Synthesis of aromatic heterocycles

Gilchrist¹

1999

J. Chem. Soc., Perkin Trans. 1

200

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“…Therefore one must conclude that RCM is complementary to the existing arsenal and exerts a significant impact on basic concepts of retrosynthetic logic. [58] Though much less established, the metathesis of alkynes in general, and the only recently discovered ring-closing metathesis of diynes (RCAM) [34] in particular, also hold great promise for target-oriented synthesis, not least because of the exceedingly high tolerance of the available catalysts. The approach to sophorolipid lactone, together with several other applications from this laboratory, [59,60] bear witness to this notion and may encourage more extensive uses of this versatile methodology in advanced organic synthesis.…”

Section: Discussionmentioning

confidence: 99%

Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

Fürstner

2004

Eur J Org Chem

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Novel strategies for the synthesis of structurally complex macrocyclic glycolipids are outlined which have opened concise and highly flexible entries into various resin glycosides and sugar-based macrodiolides. The key design elements consist of either a ring-closing alkene (RCM) or alkyne metathesis (RCAM) event or a newly developed template-directed dilactonization reaction. The performance and excellent application profile of these transformations are illustrated by the total syntheses of tricolorin A and G, woodrosin I, sophorolipid lactone, cycloviracin B₁, glucolipsin A, and various analogues thereof. A brief survey of the biological activities exerted by these amphiphilic natural products is provided

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“…[42] An identicals trategy was used to prepare ircinin-4( 111)f rom vinyl epoxide 112 and bromide 113 (Scheme 25, bottom). [43] Lastly,T anaka utilized ab is(sulfone) linker to construct the deuterium-labeled isocarbacyclin derivative 106 (Scheme 26). The ester side chain wasi nstalled by Michael addition of BPSM (4)t om ethyl acrylate and the resulting fragment was appended to the prostaglandin core using aP d-catalyzed allylic alkylation with allylic carbonate 115.…”

Section: Secondary Carbon Synthonsmentioning

confidence: 99%

“…After construction of the furan, the second half of the molecule was installed by reduction to the monosulfone, followed by deprotonation and alkylation with allylic bromide 110 (Scheme , top) . An identical strategy was used to prepare ircinin‐4 ( 111 ) from vinyl epoxide 112 and bromide 113 (Scheme , bottom) …”

Section: Synthetic Equivalents Of Sp3 Synthonsmentioning

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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Palladium Catalyzed Synthesis of the Furanoterpene Ircinin-4

Cited by 27 publications

References 10 publications

Synthesis of aromatic heterocycles

Synthesis of aromatic heterocycles

Total Syntheses and Biological Assessment of Macrocyclic Glycolipids

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

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