Carbohydrate Derived α,β-Unsaturated Enals (Perlin’s Aldehyde) as Chiral Synthon for the Synthesis of Privileged Scaffolds

References

1. TolstikovA.G. KhakhalinaN.V. SpirikhinL.V. Benzyl esters of D- and L-Arabinals as chiral synthons in organic synthesis.Synthesis19881988322122210.1055/s‑1988‑27518
   [Google Scholar]
2. McLaughlinM.J. HsungR.P. Total syntheses of pyranoquinoline alkaloids: Simulenoline, huajiaosimuline, and (+/-)-7-demethoxyzanthodioline.J. Org. Chem.20016631049105310.1021/jo001368h 11430073
   [Google Scholar]
3. LeeY.R. KweonH.I. KohW.S. MinK.R. KimY. LeeS.H. One-pot preparation of pyranoquinolinones by ytterbium(III) trifluoromethanesulfonate-catalyzed reactions: Efficient synthesis of flindersine, N-methylflindersine, and zanthosimuline natural products.Synthesis20012001121851185510.1055/s‑2001‑17516
   [Google Scholar]
4. ColemanM.A. BurchillL. SumbyC.J. GeorgeJ.H. Biomimetic synthesis enables the structure revision of furoerioaustralasine.Org. Lett.201921218776877810.1021/acs.orglett.9b03392 31603336
   [Google Scholar]
5. SagarR. ParkJ. KohM. ParkS.B. Diastereoselective synthesis of polycyclic acetal-fused pyrano[3,2-c]pyran-5(2H)-one derivatives.J. Org. Chem.20097452171217410.1021/jo8023889 19193119
   [Google Scholar]
6. SagarR. ParkS.B. Facile and efficient synthesis of carbohybrids as stereodivergent druglike small molecules.J. Org. Chem.20087383270327310.1021/jo800190v 18351781
   [Google Scholar]
7. SagarR. KimM.J. ParkS.B. An improved synthesis of pyrimidine- and pyrazole-based acyclo-C-nucleosides as carbohybrids.Tetrahedron Lett.200849345080508310.1016/j.tetlet.2008.06.032
   [Google Scholar]
8. GonzalezF. LesageS. PerlinA.S. Catalysis by mercuric ion of reactions of glycals with water.Carbohydr. Res.197542226727410.1016/S0008‑6215(00)84269‑X
   [Google Scholar]
9. TamS.Y.K. Fraser-ReidB. The formation of α, β-unsaturated aldehydes in the hydrolysis of acetylated glycals.Carbohydr. Res.1975451294310.1016/S0008‑6215(00)85863‑2
   [Google Scholar]
10. ReddyL.V.R. KumarV. SagarR. ShawA.K. Glycal-derived δ-hydroxy α, β-unsaturated aldehydes (Perlin aldehydes): Versatile building blocks in organic synthesis.Chem. Rev.201311353605363110.1021/cr200016m 23419115
    [Google Scholar]
11. TolstikovA.G. TolstikovG.A. Unsaturated sugars in enantiospecific synthesis of natural low-molecular bioregulators and their structural analogues.Bioorg. Khim.2007331727 17375656
    [Google Scholar]
12. YadavY. TyagiR. YadavK. TiwariG. SagarR. Reinvestigation of SnCl4 catalyzed efficient synthesis of 2,3-unsaturated glycopyranosides.Carbohydr. Res.202353410898910.1016/j.carres.2023.108989 38016255
    [Google Scholar]
13. TolstikovA.G. KhakhalinaN.V. OdinokovV.N. KhalilovV.M. SpirikhinL.V. TolstikovG.A. Glycals in stereospecific synthesis. I. Synthesis of (+)-cis-disparlure, the sex pheromone of the gypsy moth.Zh. Org. Khim.198925296299
    [Google Scholar]
14. TolstikovA.G. ProkopenkoO.F. KhalilovL.M. OdinokovV.N. TolstikovG.A. Glycals in stereospecific synthesis. V. Chiral synthons for 13(R), 15(R)-lipoxine B and (-)-cis-disparlure from 6-substituted 6-desoxy-D-galactose.Zh. Org. Khim199127798802
    [Google Scholar]
15. TolstikovA.G. KhakhalinaN.V. TolstikovG.A. SpirikhinL.V. KhalilovV.M. PanasenkoA.A. OdinokovV.N. Enantiospecific synthesis of (5R,6R)-6-acetoxy-5-hexadecanolide - a stereoisomer of oviposition attractant pheromone of the mosquito Culex pipiens fatigans.Bioorg. Khim.199218737739
    [Google Scholar]
16. TolstikovA.G. KhakhalinaN.V. SavateevaE.E. SpirikhinL.V. OdinokovV.N. TolstikovG.A. Glycals in stereospecific synthesis. II. Di-O-benzyl-L-arabinal and di-O-benzoyl-L-arabinal in the synthesis of saturated and unsaturated terminal epoxides.Zh. Org. Khim.198925787791
    [Google Scholar]
17. Rama RaoA.V. PurandareA.V. ReddyE.R. GurjarM.K. Synthesis of R(+)-α-lipoic acid.Synth. Commun.19871791095110210.1080/00397918708078791
    [Google Scholar]
18. TolstikovA.G. KhakhalinaN.V. SavateevaE.E. SpirikhinL.V. KhalilovL.M. OdinokovV.N. TolstikovG.A. Enantiospecific synthesis of methyl esters of R-(+)-x-lipoic acid and its optical antipode.Bioorg. Khim.19901616701674
    [Google Scholar]
19. HirataN. YamagiwaY. KamikawaT. A convenient stereoselective synthesis of D-erythro-C18-sphingosine from galactal.J. Chem. Soc.1991922792280
    [Google Scholar]
20. HerdeisC. KüpperP. PléS. An expeditious stereoselective synthesis of natural (-)-Cassine via cascade HWE [3 + 2]-cycloaddition process.Org. Biomol. Chem.20064352452910.1039/B516888K 16446811
    [Google Scholar]
21. RajanR. WallimannK. VasellaA. PaceD. GenazzaniA.A. CanonicoP.L. CondorelliF. Synthesis of 7-oxasphingosine and -ceramide analogues and their evaluation in a model for apoptosis.Chem. Biodivers.20041111785179910.1002/cbdv.200490134 17191816
    [Google Scholar]
22. KokatlaH.P. SagarR. VankarY.D. Stereoselective synthesis of safingol and its natural stereoisomer from d-glycals.Tetrahedron Lett.200849324728473010.1016/j.tetlet.2008.05.112
    [Google Scholar]
23. WalczakK. PedersenE.B. Synthesis of 3-(1,2,4-Triazol-1-yl)-2,3-dideoxy-D- arabino -hexopyranosyl and 3-(1,2,4-Triazol-1-yl)-2,3-dideoxy-D- ribo -hexofuranosyl uracils via an α, β-unsaturated aldehydohexose.Synthesis199119911195996210.1055/s‑1991‑26616
    [Google Scholar]
24. WengelJ. PedersenE.B. VestergaardB.F. Synthesis of 2′,3′-Dideoxy-3′-piperidino- and 2′, 3′-Dideoxy-3′-pyrrolidino-D- ribo -hexofuranosyl Nucleosides from Tri- O -acetyl-D-glucal.Synthesis19921992331932210.1055/s‑1992‑26100
    [Google Scholar]
25. TurnerC.I. WilliamsonR.M. TurnerP. SherburnM.S. The domino intramolecular Diels–Alder approach to 16-oxasteroids.Chem. Commun. (Camb.)200313131610161110.1039/B303362G
    [Google Scholar]
26. GalánE.R. ChamizoM.J. SerranoJ.A. Diels-Alder reactions with an α, β-unsaturated aldehydo-sugar. A route to 6-oxabicyclo[3.2.1]octanes.Tetrahedron Lett.199334111811181410.1016/S0040‑4039(00)60786‑4
    [Google Scholar]
27. SagarR. SinghP. KumarR. MaulikP.R. ShawA.K. Diastereoselective annulation of 4-hydroxypyran-2H-ones with enantiopure 2,3-dideoxy-α, β-unsaturated sugar aldehydes derived from respective glycals.Carbohydr. Res.200534071287130010.1016/j.carres.2005.02.018 15854598
    [Google Scholar]
28. SydorenkoN. HsungR.P. VeraE.L. Torquoselective 6π-electron electrocyclic ring closure of 1-azatrienes containing acyclic chirality at the C-terminus.Org. Lett.20068122611261410.1021/ol060932t 16737326
    [Google Scholar]
29. GhoshS.K. BuchananG.S. LongQ.A. WeiY. Al-RashidZ.F. SklenickaH.M. HsungR.P. Aza- and carbo-[3+3] annulations of exo-cyclic vinylogous amides and urethanes. Synthesis of tetrahydroindolizidines and an unexpected formation of hexahydroquinolines.Tetrahedron200864588389310.1016/j.tet.2007.09.089 19180170
    [Google Scholar]
30. ArecesP. CarrascoE. MonterdeM. LightM.E. PlumetJ. Synthesis of optically pure 4-hydroxymethyl-3-phenoxy-2-azetidinone from D-glucal.J. Heterocycles20077385786210.3987/COM‑07‑S(U)18
    [Google Scholar]
31. PathakR. ShawA.K. BhaduriA.P. Syntheses of Tri- and Tetrahydroxylated 1-Amino-Heptanes.Synth. Commun.200030193595360510.1080/00397910008087276
    [Google Scholar]
32. PathakR. ShawA.K. BhaduriA.P. ChandrasekharK.V.G. SrivastavaA. SrivastavaK.K. ChaturvediV. SrivastavaR. SrivastavaB.S. AroraS. SinhaS. Higher acyclic nitrogen containing deoxy sugar derivatives: A new lead in the generation of antimycobacterial chemotherapeutics.Bioorg. Med. Chem.20021061695170210.1016/S0968‑0896(02)00045‑7 11937328
    [Google Scholar]
33. SagarR. PathakR. ShawA.K. Reinvestigation of the mercuration–demercuration reaction on alkylated glycals: An improved method for the preparation of 2,3-dideoxy-α, β-unsaturated carbohydrate enals.Carbohydr. Res.2004339112031203510.1016/j.carres.2004.05.027 15261597
    [Google Scholar]
34. SaquibM. SagarR. ShawA.K. An efficient synthesis of 2,3-dideoxy-α, β-unsaturated carbohydrate enals by mixed Lewis acid (HfCl4 and ZnI2) catalyzed hydration of glycals.Carbohydr. Res.200634181052105610.1016/j.carres.2006.02.031 16564512
    [Google Scholar]
35. NagarajP. GanesanM. RameshN.G. InCl3–CH3CN–H2O: an efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars.Tetrahedron201167476977610.1016/j.tet.2010.11.050
    [Google Scholar]
36. SinghK. BeheraS.S. TyagiR. TiwariG. SagarR. Metal free synthesis of 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes).Carbohydr. Res.202353110889010.1016/j.carres.2023.108890 37406515
    [Google Scholar]
37. HalderS. MoktanS. SreeramV. KancharlaP.K. Synthesis of chiral functional polyhydroxylated arenes via Mukaiyama aldol reaction from Perlin aldehydes.Carbohydr. Res.202453510900410.1016/j.carres.2023.109004 38091696
    [Google Scholar]
38. HalderS. AddankiR.B. KancharlaP.K. Three-step synthesis of protected L-altrose from D-galactose derived Perlin aldehyde.J. Indian Chem. Soc.202097243250
    [Google Scholar]
39. VankarY. RajasekaranP. MallikharjunaraoY. Synthesis of 1C-Aryl/Alkyl 2C-branched sugar-fused isochroman derivatives by sequential prins and friedel–crafts cyclizations on a perlin aldehyde derived substrate.Synlett201728111346135210.1055/s‑0036‑1588156
    [Google Scholar]
40. MadhubabuT. YousufS.K. KusunuruA.K. MukherjeeD. Transformation of glycals into α, β,γ,δ‐conjugated chirons under metal‐free conditions.Eur. J. Org. Chem.20142014337333733810.1002/ejoc.201403041
    [Google Scholar]
41. DasP. KundooruS. ShawA.K. ‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent.RSC Advances2016618145051451110.1039/C5RA27342K
    [Google Scholar]
42. KundooruS. DasP. MeenaS. KumarV. SiddiqiM.I. DattaD. ShawA.K. Substrate and stereocontrolled iodocycloetherification of highly functionalized enantiomerically pure allylic alcohols: Application to synthesis of cytotoxic 2-epi jaspine B and its biological evaluation.Org. Biomol. Chem.201513308241825010.1039/C5OB01123J 26133669
    [Google Scholar]
43. DubbuS. BardhanA. ChennaiahA. VankarY.D. A cascade of prins reaction and pinacol‐type rearrangement: Access to 2,3‐Dideoxy‐3C‐Formyl β‐C‐Aryl/Alkyl Furanosides and 2‐Deoxy‐2C‐Branched β‐C‐Aryl Furanoside.Eur. J. Org. Chem.20182018476800680810.1002/ejoc.201801318
    [Google Scholar]
44. WilliamR. WangS. DingF. ArvianaE.N. LiuX.W. Interrupted imino-Nazarov cyclization of 1-aminopentadienyl cation and related cascade process.Angew. Chem. Int. Ed.20145340107421074610.1002/anie.201405251 25112885
    [Google Scholar]
45. AlblerC. HollausR. KähligH. SchmidW. Indium-mediated allylation in carbohydrate synthesis: A short and efficient approach towards higher 2-acetamido-2-deoxy sugars.Beilstein J. Org. Chem.2014102230223410.3762/bjoc.10.231 25246982
    [Google Scholar]
46. MalK. SharmaA. DasI. Gold(III) chloride catalyzed synthesis of chiral substituted 3-formyl furans from carbohydrates: application in the synthesis of 1,5-dicarbonyl derivatives and furo[3,2-c]pyridine.Chemistry20142037119321194510.1002/chem.201402286 25077819
    [Google Scholar]
47. KinfeH.H. MebrahtuF.M. MakoloF.L. MoshapoP.T. MananaM.M. Stereoselective synthesis of thiochromenes via intramolecular tandem thio-Michael addition of in situ generated α, β-unsaturated aldehydes.J. Org. Chem.20147973111311810.1021/jo5002164 24606120
    [Google Scholar]
48. SinghB.K. KumarS. AroraA. KumarS. KumariP. SinghS.K. Diastereoselective synthesis of carbohydrate conjugates: Pyrano[3,2-c]quinolones.Synthesis20245671157116610.1055/s‑0042‑1751505
    [Google Scholar]
49. AroraI. KashyapV.K. SinghA.K. DasguptaA. KumarB. ShawA.K. Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: Conformational constraint as an effective tool for tailoring the selectivity of α-glucosidase inhibitors.Org. Biomol. Chem.201412356855686810.1039/C4OB00486H 25050482
    [Google Scholar]