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Application of butane-2,3-diacetals in the synthesis of optically active natural products
Języki publikacji
Abstrakty
Butanodiacetale (BDA) są stabilnymi, optycznie czynnymi blokami budulcowymi wykorzystywanymi w syntezie produktów naturalnych. Otrzymać je można na drodze syntezy z tanich substratów: D-mannitolu, kwasu L-askorbinowego, L-winianu dimetylowego, oraz D-winianu dimetylowego. Usztywniona struktura butanodiacetali daje możliwość zastosowania ich w syntezie asymetrycznej. Przedstawiono przegląd literaturowy dotyczący syntezy butanodiacetali oraz ich zastosowania do syntezy małocząsteczkowych i wielkocząsteczkowych naturalnych związków optycznie czynnych.
Butane diacetals (BDAs) are stable, optically active building blocks used in the synthesis of natural products. They can be synthesized from cheap substrates such as: D-mannitol, L-ascorbic acid, dimethyl L-tartrate and dimethyl D-tartrate. The rigid structure of butane diacetals makes possible their application in asymmetric synthesis. The article presents literature review on synthesis of butane diacetals and their application in the synthesis of natural small and large optically active compounds.
Czasopismo
Rocznik
Tom
Strony
304--311
Opis fizyczny
Bibliogr. 29 poz., rys.
Twórcy
autor
- Wydział Chemii, Uniwersytet Opolski, Opole
autor
- Wydział Chemii, Uniwersytet Opolski, Opole
autor
- Wydział Chemii, Uniwersytet Opolski, Opole
Bibliografia
- 1. D. K., Dixon D. J., Foster A. C., Ince S. J., Priepke H. W. M., Reynolds D. J.: 1,2-Diacetals: A new opportunity for organic synthesis. Chem. Rev. 2001, 101, 53–80.
- 2. Ley S. V., Polara A.; A Fascination with 1,2-Diacetals. J. Org. Chem. 2007, 72, 5943–5959.
- 3. Lence E., Castedo L., Gonzalez-Bello C.: The conformational rigidity of butane-1,2-diacetals as a powerful synthetic tool. Chem. Soc. Rev. 2008, 37, 1689–1708.
- 4. Ley S. V., Woods M., Zanotti-Gerosa A.: Dispiroketals in synthesis: Preparation of a stable, sterically demanding glyceraldehyde ketal and diastereoselective reactions with simple organometallic reagents. Synthesis 1992, 52–54.
- 5. Michel P., Ley S. V.: Butane-2,3-diacetals of glyceraldehyde: A stable alternative to glyceraldehyde acetonide. Angew. Chem. Int. Ed. 2002, 41, 3898–3901.
- 6. Jurczak J., Pikul S., Bauer S.: (R)- and (S)-2,3‒0-isopropylideneglyceraldehyde in stereoselective organic synthesis. Tetrahedrn, 1986, 42, 447–488.
- 7. Ley S. V., Michel P.: Preparation of butane-1,2-diacetal-protected L-glyceraldehyde from D-mannitol. Synthesis 2004, 147–150.
- 8. Michel P., Ley S. V.: Synthesis of enantiomers of butane-1,2-diacetal-protected glyceraldehyde and of (R,R)-butane-1,2-diacetal-protected glycolic acid. Synthesis 2003, 1598–1602.
- 9. Barlow J. S., Dixon D. J., Foster A. C., Ley S. V., Reynolds D. J.: New building blocks for efficient and highly diastereoselective polyol production – synthesis and utility of (R’,R’,S,S) and (S’,S’,R,R)-2,3-butane diacetal protected butane tetrol derivatives. J. Chem. Soc. Perkin Trans. 1 1999, 1627–1629.
- 10. Dixon D. J., Foster A. C., Ley S. V.: The total synthesis of (+)-aspicilin using 2,3-butane diacetal protected butane tetrols via a chiral memory protocol. Can. J. Chem. 2001, 79, 1668–1680.
- 11. Ley S. V., Michel P., Trapella C.: A convenient route to enantiomerically pure 2-substituted methyl glycerate derivatives. Org. Lett. 2003, 5, 4553–4555.
- 12. Pohmakotr M., Kambutong S., Tuchinda P., Kuhakarn C.: Asymmetric synthesis of pentenomycin I, epipentenomycin I, and their analogs. Tetrahedron 2008, 64, 6315–6323.
- 13. Mahapatra S., Carter R. G.: Efficient synthesis of the C7-C20 subunit of amphidinolides C and F. Org. Biomol. Chem. 2009, 7, 4582–4585.
- 14. Boyer J., Allenbach Y., Ariza X., Garcia J., Georges Y., Vicente M.: New stereoselective approach to 1,2,3-triols: Application to a straightforward access to polyoxamic acid array. Synlett 2006, 1895–1898.
- 15. Diez E., Dixon D. J., Ley S. V.: Butane-2,3-Diacetal-Desymmetrized Glycolic Acid – A New Building Block for the Stereoselective Synthesis of Enantiopure α-Hydroxy Acid. Angew. Chem. Int. Ed. 2001, 40, 2906–2909.
- 16. Dixon D. J., Ley S. V., PolaraA, Sheppard T.: Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters. Org. Lett. 2001, 3, 3749–3752.
- 17. Diez E., Dixon D. J. Ley S. V. Polara A., Rodriguez F.: The use of butane diacetals of glycolic acid as precursors for the synthesis of the phytotoxic calmodulin inhibitor herbarumin II. Helv. Chim. Acta 2003, 86, 3717–3729.
- 18. Ley S. V., Tackett M. N., Maddess M. L., Anderson J. C., Brennan P. E., Cappi M. W., Heer J. P., Helgen C., Kori M., Kouklovsky C., Marsden S. P., Norman J., Osborn D. P., Palomero M. A., Pavey J. B. J., Pinel C., Robinson L. A., Schnaubelt J., Scott J. S., Spilling C. D., Watanabe H., Wesson K. E., Willis M.C: Total Synthesis of Rapamycin. Chem. Eur. J. 2009, 15, 2874–2914.
- 19. Dixon D. J., Ley S. V., Lohmann S., Sheppard T. D.: Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks. Synlett 2005, 481–484.
- 20. Nattrass G. L., Diez E., McLachlan M. M., Dixon D. J., Ley S.V.: The total synthesis of the annonaceous acetogenin 10-hydroxyasimicin. Angew. Chem. Int. Ed. 2005, 44, 580–584.
- 21. Brittain D. E. A., Griffiths-Jones C. M., Linder M. R., Smith M. D., McCusker C., Barlow J. S., Akiyama R., Yasuda K., Ley S. V.: Total synthesis of antascomicin B. Angew. Chem. Int. Ed. 2005, 44, 2732–2737.
- 22. Dixon D. J., Foster A. C., Ley S. V., Reynolds D. J.: A general and efficient procedure for the preparation of enantiopure anti-1,2-diols – synthesis and utility of (R’,R’,S,R)-2,3-butane diacetal protected butane tetrol. J. Chem. Soc. Perkin Trans. 1 1999, 1635–1637.
- 23. Dixon D. J., Ley S. V., Reynolds D. J.: The total synthesis of the annonaceous acetogenin,muricatetrocin C. Chem. Eur. J. 2002, 8, 1621–1636.
- 24. Kiyota H., Dixon D. J., Luscombe C. K., Hettstedt S., Ley S. V.: Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp. Org. Lett. 2002, 4, 3223–3226.
- 25. Woodhall T., Williams G., Berry A., Nelson A.: Synthesis of screening substrates for the directed evolution of sialic acid aldolase: towards tailored enzymes for the preparation of influenza A sialidase inhibitor analogues. Org. Biomol. Chem. 2005, 3, 1795–1800.
- 26. Shih T.-L., Wu S.-H.: Efficient syntheses of (-)-shikimate and (-)-quinate 3-phosphate via trans vicinal diol protection with 2,2,3,3-tetramethoxybutane (TMB) of shikimic and quinic acids. Tetrahedron Lett. 2000, 41, 2957–2959.
- 27. Austin K. A. B., Banwell M. G., Loong D. T. J., Rae A. D., Willis A. C.: A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide B via a mid-stage ring-closing metathesis and a late-stage photo-rearrangement of the E-isomer. Org. Biomol. Chem. 2005, 3, 1081–1088.
- 28. Barros M. T., Maycock C. D., Ventura M. R.: Aldol reactions of dioxanes derived from tartaric acid. A total synthesis of (+)-nephrosteranic acid. Org. Lett. 2003, 5, 4097–4099.
- 29. Tzschucke C. C., Pradidphol N., Dieguez-Vazquez A., Kongkathip B., Kongkathip N., Ley S. V.: FeCl3-catalysed cleavage of 1,2-butanediacetal protected diols. Synlett 2008, 1293–1296.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-53042504-d735-4ac7-88a4-d5caa709ca38