Synthetic approaches towards structurally diverse γ-butyrolactone natural-product-like compounds

Current Opinion in Chemical Biology

Volumn 9, Issue 3, 2005, Pages 285-292

  Seitz, Michael ^a   Reiser, Oliver ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; NATURAL PRODUCT; ORGANIC COMPOUND; TRANSITION ELEMENT;

CATALYSIS; CATALYST; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

4-BUTYROLACTONE; BIOLOGICAL FACTORS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; DRUG DESIGN; MOLECULAR STRUCTURE;

EID: 20444404268     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpa.2005.03.005     Document Type: Review

References (45)

1. H.M.R. Hoffmann, and J. Rabe Synthesis and biological activity of α-methylene-γ-butyrolactones Angew Chem Int Ed Engl 24 1985 94 110
2. S.S.C. Koch, and A.R. Chamberlin Enantiomerically pure gamma-butyrolactones in natural products synthesis Atta-ur-Rahman Studies in Natural Products Chemistry, Vol. 16 1995 Elsevier Science 687 725
3. T.E. Shaikenov, S.M. Adekenov, R.M. Williams, F.L. Baker, N. Prashad, T.L. Madden, and R. Newman Arglabin-DMA, a plant derived sesquiterpene inhibits farnesyltransferase Oncol Rep 8 2001 173 179
4. E.-i. Negishi, and M. Kotora Regio- and stereoselective synthesis of γ-alkylidenebutenolides and related compounds Tetrahedron 53 1997 6707 6738
5. I. Collins Saturated and unsaturated lactones J Chem Soc, Perkin Trans 1 1998 1869 1888
6. R. Bandichhor, B. Nosse, and O. Reiser Paraconic acids - the natural products from lichen symbiont Top Curr Chem 243 2005 43 72
7. P. Arya, D.T.H. Chou, and M.-G. Baek Diversity-based organic synthesis in the era of genomics and proteomics Angew Chem Int Ed Engl 40 2001 339 346
8. D.G. Hall, S. Manku, and F. Wang Solution- and solid-phase strategies for the design, synthesis, and screening of libraries based on natural product templates: A comprehensive survey J Comb Chem 3 2001 125 150
9. U. Abel, C. Koch, M. Speitling, and F.G. Hansske Modern methods to produce natural-product libraries Curr Opin Chem Biol 6 2002 453 458
10. P. Arya, R. Joseph, and D.T.H. Chou Toward high-throughput synthesis of complex natural product-like compounds in the genomics and proteomics age Chem Biol 9 2002 145 156 Insightful review, giving a critical account on synthetic strategies towards natural product libraries.
11. K. Knepper, C. Gil, and S. Bräse Natural product-like and other biologically active heterocyclic libraries using solid-phase techniques in the post-genomic era Comb Chem High Throughput Screen 6 2003 673 691
12. D. Hoppe, and T. Hense Enantioselective synthesis with lithium/(-)-sparteine carbanion pairs Angew Chem Int Ed Engl 36 1997 2283 2316
13. M. Özlugedik, J. Kristensen, J. Reuber, R. Frohlich, and D. Hoppe Stereoselective synthesis of highly substituted bicyclic γ-lactones using homoaldol addition of 1-(1-cycloalkenyl)methyl carbamates Synthesis 2004 2303 2316 This work gives the latest account on the wide range of γ-butyrolactones accessible by the homoaldol process by stereoselective deprotonation of alkenyl carbamates.
14. •].
15. •] describe organocatalysts that allow the direct coupling of enals and aldehydes by conjugate umpolung to give rise directly to γ-butyrolactones.
16. F. Schleth, T. Vogler, K. Harms, and A. Studer Stereoselective synthesis of (+)-trans-whisky lactone using chiral cyclohexadienyl Ti compound Chem Eur J 10 2004 4171 4185
17. S.-i. Fukuzawa, M. Miura, and T. Saitoh One-step highly diastereoselective synthesis of γ-butyrolactones by an asymmetric samarium-mediated ketyl-alkene coupling reaction J Org Chem 68 2003 2042 2044
18. S.-i. Fukuzawa, K. Seki, M. Tatsuzawa, and K. Mutoh A facile synthesis of chiral γ-butyrolactones in extremely high enantioselectivity mediated by samarium(II) iodide J Am Chem Soc 119 1997 1482 1483
19. D.J. Spielvogel, and S.L. Buchwald Nickel-BINAP catalyzed enantioselective α-arylation of α-substituted γ-butyrolactones J Am Chem Soc 124 2002 3500 3501
20. M.T. Barros, A.J. Burke, J.-D. Lou, C.D. Maycock, and J.R. Wahnon Highly stereoselective aldol reaction for the synthesis of γ-lactones starting from tartaric acid J Org Chem 69 2004 7847 7850
21. M.P. Sibi, J. Lu, and C.L. Talbacka Enantiospecific synthesis of trisubstituted butyrolactone natural products and their analogs J Org Chem 61 1996 7848 7855
22. D.A. Evans, J. Wu, C.E. Masse, and D.W.C. MacMillan A general method for the enantioselective synthesis of pantolactone derivatives Org Lett 4 2002 3379 3382
23. B.M. Trost, and Y.H. Rhee Ruthenium-catalyzed cycloisomerization- oxidation of homopropargyl alcohols. A new access to γ-butyrolactones J Am Chem Soc 121 1999 11680 11683
24. M.-J. Chen, C.-Y. Lo, C.-C. Chin, and R.-S. Liu Total synthesis of (+)-blastmycinone, (-)-litsenolide C1, and related natural trisubstituted lactones via alkynyltungsten compounds J Org Chem 65 2000 6362 6367
25. S.V. Gagnier, and R.C. Larock Palladium-catalyzed heteroannulation of 1,3-dienes to form α-alkylidene-γ-butyrolactones J Org Chem 65 2000 1525 1529
26. Q. Zhang, and X. Lu Highly enantioselective palladium(II)-catalyzed cyclization of (Z)-4′-acetoxy-2′-butenyl 2-alkynoates: an efficient synthesis of optically active γ-butyrolactones J Am Chem Soc 122 2000 7604 7605
27. H.M.L. Davies, and R.E.J. Beckwith Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion Chem Rev 103 2003 2861 2903
28. M.P. Doyle, J.S. Tedrow, A.B. Dyatkin, C.J. Spaans, and D.G. Ene Enantioselective syntheses of 2-deoxyxylono-1,4-lactone and 2-deoxyribono-1,4- lactone from 1,3-dioxan-5-yl diazoacetates J Org Chem 64 1999 8907 8915
29. J.W. Bode, M.P. Doyle, M.N. Protopopova, and Q.-L. Zhou Intramolecular regioselective insertion into unactivated prochiral carbon-hydrogen bonds with diazoacetates of primary alcohols catalyzed by chiral dirhodium(II) carboxamidates. Highly enantioselective total synthesis of natural lignan lactones J Org Chem 61 1996 9146 9155
30. N.M. Kablaoui, F.A. Hicks, and S.L. Buchwald Titanocene-catalyzed cyclocarbonylation of o-allyl aryl ketones to γ-butyrolactones J Am Chem Soc 119 1997 4424 4431
31. S.K. Mandal, S.R. Amin, and W.E. Crowe γ-Butyrolactone synthesis via catalytic asymmetric cyclocarbonylation J Am Chem Soc 123 2001 6457 6458
32. S.-K. Kang, K.-J. Kim, and Y.-T. Hong Synthesis of α-methylene- γ-butyrolactones: Ru-catalyzed cyclocarbonylation of allenyl aldehydes and allenyl ketones Angew Chem Int Ed Engl 41 2002 1584 1586
33. N. Chatani, M. Tobisu, T. Asaumi, Y. Fukumoto, and S. Murai Ruthenium carbonyl-catalyzed [2+2+1]-cycloaddition of ketones, olefins, and carbon monoxide, leading to functionalized γ-butyrolactones J Am Chem Soc 121 1999 7160 7161
34. E.A. Bercot, D.E. Kindrachuk, and T. Rovis Complementary diastereoselective reduction of cyclic γ-keto acids: efficient access to trisubstituted γ-lactones Org Lett 7 2005 107 110
35. Z.-H. Peng, and K.A. Woerpel Stereoselective synthesis of substituted γ-butyrolactones by the [3+2] annulation of allylic silanes with chlorosulfonyl isocyanate: enantioselective total synthesis of (+)-blastmycinone Org Lett 3 2001 675 678
36. S.P. Brown, N.C. Goodwin, and D.W.C. MacMillan The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched γ-butenolide architecture J Am Chem Soc 125 2003 1192 1194
37. C. Harcken, and R. Brückner Synthesis of optically active butenolides and γ-lactones by the Sharpless asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters Angew Chem Int Ed Engl 36 1997 2750 2752
38. B.L. Feringa, B. de Lange, and J.C. de Jong Synthesis of enantiomerically pure γ-(menthyloxy)butenolides and (R)- and (S)-2-methyl-1,4-butanediol J Org Chem 54 1989 2471 2475
39. B.M. Trost, and M.L. Crawley A "chiral aldehyde" equivalent as a building block towards biologically active targets Chem Eur J 10 2004 2237 2252 A practical protocol to a chiral butenolide is described, which can be subsequently used in many different reactions to give γ-butyrolactones with great structural diversity.
40. C. Böhm, M. Schinnerl, C. Bubert, M. Zabel, T. Labahn, E. Parisini, and O. Reiser A new strategy for the stereoselective synthesis of 1,2,3-trisubstituted cyclopropanes Eur J Org Chem 2000 2955 2965
41. C. Böhm, and O. Reiser Enantioselective synthesis of (-)-roccellaric acid Org Lett 3 2001 1315 1318
42. R.B. Chhor, B. Nosse, S. Soergel, C. Böhm, M. Seitz, and O. Reiser Enantioselective synthesis of paraconic acids Chem Eur J 9 2003 260 270
43. B. Nosse, R.B. Chhor, W.B. Jeong, C. Böhm, and O. Reiser Facile asymmetric synthesis of the core nuclei of xanthanolides, guaianolides, and eudesmanolides Org Lett 5 2003 941 944
44. E. Jezek, A. Schall, P. Kreitmeier, and O. Reiser Radical cyclizations as key step for the stereoselective synthesis of bi- and tricyclic sesquiterpene lactones Synlett 2005 15 918
45. D.S. Tan, M.A. Foley, B.R. Stockwell, M.D. Shair, and S.L. Schreiber Synthesis and preliminary evaluation of a library of polycyclic small molecules for use in chemical genetic assays J Am Chem Soc 121 1999 9073 9087