The piancatelli rearrangement: New applications for an intriguing reaction

Molecules

Volumn 18, Issue 10, 2013, Pages 12290-12312

  Piutti, Claudia ^a   Quartieri, Francesca ^a  

^a NERVIANO MEDICAL SCIENCES   (Italy)

Author keywords

2 furylcarbinols; Domino reaction; Pentadienyl cation; Prostaglandins; Spirocycles

Indexed keywords

4 HYDROXYCYCLOPENTENONE; 4-HYDROXYCYCLOPENTENONE; APREPITANT; CYCLOPENTANE DERIVATIVE; FURAN DERIVATIVE; FURFURYL ALCOHOL; MORPHOLINE DERIVATIVE; NEUROKININ 1 RECEPTOR ANTAGONIST; PROSTAGLANDIN; SARGAFURAN; TERPENE;

ALKYLATION; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; HUMAN; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALKYLATION; CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLOPENTANES; FURANS; HUMANS; MODELS, CHEMICAL; MORPHOLINES; NEUROKININ-1 RECEPTOR ANTAGONISTS; PROSTAGLANDINS; STEREOISOMERISM; TERPENES;

EID: 84886635011     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181012290     Document Type: Review

References (69)

1. Piancatelli, G.; Scettri, A. Heterocyclic steroids-III: The synthetic utility of a 2-Furyl steroid. Tetrahedron 1977, 33, 69-72.
2. Piancatelli, G.; Scettri, A.; Barbadoro, S. A useful preparation of 4-Substituted-5-hydroxy-3-oxocyclopentene. Tetrahedron Lett. 1976, 17, 3555-3558.
3. Spencer, W.T.; III; Vaidya, T.; Frontier, A.J. Beyond the divinyl ketone: Innovations in the generation and nazarov cyclization of pentadienyl cation intermediates. Eur. J. Org. Chem. 2013, 3621-3633.
4. Habermas, K.L.; Denmark, S.E.; Jones, T.K. The nazarov cyclization. In Org. React.; Paquette, L.A., Ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2004; Volume 45, pp. 1-158.
5. Davis, R.L.; Tantillo, D.J. Theoretical studies on pentadienyl cation electrocyclizations. Curr. Org. Chem. 2010, 14, 1561-1577.
6. Nieto Faza, O.; Silva López, C.; Álvarez, R.; de Lera, Á.R. Theoretical study of the electrocyclic ring closure of hydroxypentadienyl cations. Chem. Eur. J. 2004, 10, 4324-4333.
7. D'Auria, M. A new simple procedure for the isomerization of 2-Furylcarbinols to cyclopentenones. Heterocycles 2000, 52, 185-194.
8. Yin, B.-L.; Wu, Y.-L.; Lai, J.-Q. Novel conversions of furandiols and spiroacetal enol ethers into cyclopentenones: Implications of the isomerization mechanism of 2-furylcarbinols into cyclopentenones. Eur. J. Org. Chem. 2009, 2695-2699.
9. Yin, B.-L.; Yang, Z.-M.; Hu, T.-S.; Wu, Y.-L. Molecular diversity of tonghaosu: synthesis of lactam-containing tonghaosu analogs. Synthesis 2003, 1995-2000.
10. Yang Gao, Y.; Wu, W.-L.; Ye, B.; Zhou, R.; Wu, Y.-L. Convenient syntheses of tonghaosu and two thiophene substituted spiroketal enol ether natural products. Tetrahedron Lett. 1996, 37, 893-896.
11. Yin, B.-L.; Wu, Y.; Wu, Y.-L. Acid catalysed rearrangement of a spiroketal enol ether. An easy synthesis of chrycorin. J. Chem. Soc. Perkin Trans. 1 2002, 1746-1747.
12. Piancatelli, G. Advances in cyclopentenone synthesis from furans. Heterocycles 1982, 19, 1735-1744.
13. Piancatelli, G.; D'Auria, M.; D'Onofrio, F. Synthesis of 1,4-Dicarbonyl compounds and cyclopentenones from furans. Synthesis 1994, 867-889.
14. Piancatelli, G.; Scettri, A.; David, G.; D'Auria, M. A new synthesis of 3-Oxocyclopentenes. Tetrahedron 1978, 34, 2775-2778.
15. D'Auria, M.; D'Onofrio, F.; Piancatelli, G.; Scettri, A. A convenient synthesis of 2-Bromo- and 3-Bromo-4-hydroxy-2-cyclopenten-1-ones. Gazz. Chim. Ital. 1986, 116, 173-175.
16. D'Auria, M.; Piancatelli, G.; Scettri, A. A useful preparation of 5-Nitro-2-furan derivatives. Tetrahedron 1980, 36, 1877-1878.
17. D'Auria, M.; Piancatelli, G.; Scettri, A. Synthesis of 4-Ylidenebutenolides and 4-Oxo-2-enoic acid methyl esters from 5-Methoxy-2-furyl carbinols. Tetrahedron 1980, 36, 3071-3074.
18. Gilman, H.; Franz, R.A.; Hewlett, A.P.; Wright, G.F. Decomposition of 5-Halogeno-2-furylmethyl ethers to benzalcrotonolactones. J. Am. Chem. Soc. 1950, 72, 3-8.
19. Antonioletti, R.; de Mico, A.; Piancatelli, G.; Scettri, A.; Ursini, O. Cyclopentenones derivatives by solvolysis of 2-Furylidene carbinols. Gazz. Chim. Ital. 1986, 116, 745-746.
20. Castagnino, E.; D'Auria, M.; de Mico, A.; D'Onofrio, F.; Piancatelli, G. Studies of the reactivity of 2-Furylhydroxymethylphosphonates: Synthesis of 1-Oxo-4-hydroxycyclopent-2-en-5-ylphosphonates. J. Chem. Soc. Chem. Commun. 1987, 907-908.
21. Saito, K.; Yamachika, H. Process for producing 3-Oxocyclopentenes. U.S. Patent 4356326, 1982.
22. Saito, K.; Yamachika, H. Process for producing 4-Hydroxycyclopentenones. U.S. Patent 4371711, 1983.
23. Saito, K.; Yamachika, H. Process for preparing cyclopentenolones. U.S. Patent 4510329, 1985.
24. Saito, K.; Takisawa, Y.; Yamachika, H. Process for preparing cyclopentenolones. U.S. Patent 4398043, 1983.
25. Ulbrich, K.; Kreitmeier, P.; Reiser, O. Microwave-or microreactor- assisted conversion of furfuryl alcohols into 4-Hydroxy-2-cyclopentenones. Synlett 2010, 13, 2037-2040.
26. Stork, G.; Kowalski, C.; Garcia, G. Route to prostaglandins via a general synthesis of 4-Hydroxycyclopentenones. J. Am. Chem. Soc. 1975, 97, 3258-3260.
27. Piancatelli, G.; Scettri, A. A simple conversion of 4-Substituted-5- hydroxy-3-Oxocyclopentenes into the 2-Substituted analogs. Synthesis 1977, 116-117.
28. Scettri, A.; Piancatelli, G.; D'Auria, M.; David, G. General route and mechanism of the rearrangement of the 4-Substituted-5-hydroxy-3-oxocyclopentenes into the 2-Substituted analogs. Tetrahedron 1979, 35, 135-138.
29. Piancatelli, G.; Scettri, A. A useful preparation of (±) t-Butyl 3-hydroxy-5-oxo-1-cyclopenteneheptanoate and its 3-Deoxy-derivative, important prostaglandin intermediates. Tetrahedron Lett. 1977, 18, 1131-1134.
30. Collins, P.W.; Kramer, S.W.; Gasiecki, A.F.; Weier, R.M.; Jones, P.H.; Gullikson, G.W.; Bianchi, R.G.; Bauer, R.F. Synthesis and gastrointestinal pharmacology of a 3E,5Z diene analog of misoprostol. J. Med. Chem. 1987, 30, 193-197.
31. Dygos, J.H.; Adamek, J.P.; Babiak, K.A.; Behling, J.R.; Medich, J.R.; Ng, J.S.; Wieczorek, J.J. An efficient synthesis of the antisecretory prostaglandin enisoprost. J. Org. Chem. 1991, 56, 2549-2552.
32. Collins, P.W.; Kramer, S.W.; Gullikson, G.W. Synthesis and gastrointestinal pharmacology of the 4-Fluoro analog of enisoprost. J. Med. Chem. 1987, 30, 1952-1955.
33. Harikrishna, M.; Mohan, H.R.; Dubey, P.K.; Subbaraju, G.V. Synthesis of 2-Normisoprostol, methyl 6-(3-hydroxy-2-((E)-4-hydroxy-4-methyloct-1-enyl)-5- oxocyclopentyl)hexanoate. Synth. Commun. 2009, 39, 2763-2775.
34. Rodríguez, A.; Nomen, M.; Spur, B.W.; Godfroid, J.-J. An efficient asymmetric synthesis of prostaglandin E1. Eur. J. Org. Chem. 1999, 1999, 2655-2662.
35. Rodríguez, A.R.; Spur, B.W. First total synthesis of the E type I phytoprostanes. Tetrahedron Lett. 2003, 44, 7411-7415.
36. Henschke, J.P.; Liu, Y.; Chen, Y.-F.; Meng, D.; Sun, T. Process for the preparation of prostaglandin analogues and intermediates thereof. U.S. Patent 2009/0259058, 2009.
37. Henschke, J.P.; Liu, Y.; Chen, Y.-F.; Meng, D.; Sun, T. Process for the preparation of prostaglandin analogues and intermediates thereof. U.S. Patent 7897795, 2011.
38. Henschke, J.P.; Liu, Y.; Huang, X.; Chen, Y.; Meng, D.; Xia, L.; Wei, X.; Xie, A.; Li, D.; Huang, Q.; et al. The manufacture of a homochiral 4-silyloxycyclopentenone intermediate for the synthesis of prostaglandin analogues. Org. Process. Res. Dev. 2012, 16, 1905-1916.
39. Peake, S.L. Bis-thiolakylfurans useful as cyclopentenon prostaglandin intermediates. U.S. Patent 4390707, 1983.
40. Paz-Otero, M.; Santín, E.P.; Rodríguez-Barrios, F.; Vaz, B.; de Lera, Á.R. Selective, potent PPAR@c agonists with cyclopentenone core structure. Bioorg. Med. Chem. Lett. 2009, 19, 1883-1886.
41. Li, C.-C.; Wang, C.-H.; Liang, B.; Zhang, X.-H.; Deng, L.-J.; Liang, S.; Chen, J.-H.; Wu, Y.-D.; Yang, Z. Synthetic study of 1,3-Butadiene-based IMDA Approach to Construct a [5-7-6] Tricyclic core and its application to the total synthesis of C8-epi-Guanacastepene O. J. Org. Chem. 2006, 71, 6892-6897.
42. Beingessner, R.L.; Farand, J.A.; Barriault, L. Progress toward the total synthesis of (±)-Havellockate. J. Org. Chem. 2010, 75, 6337-6346.
43. Katsuta, R.; Aoki, K.; Yajima, A.; Nukada, T. Synthesis of the core framework of the proposed structure of sargafuran. Tetrahedron Lett. 2013, 54, 347-350.
44. Veits, G.K.; Wenz, D.R.; Read de Alaniz, J. Versatile method for the synthesis of 4-Aminocyclopentenones: Dysprosium(III) triflate catalyzed aza-piancatelli rearrangement. Angew. Chem. Int. Ed. 2010, 49, 9484-9487.
45. Li, S.W.; Batey, R.A. Mild lanthanide (III) catalyzed formation of 4,5-Diaminocyclopent-2-enones from 2-Furaldehyde and secondary amines: A domino condensation/ring-opening/electrocyclization process. Chem. Commun. 2007, 3759-3761.
46. Veits, G.K.; Read de Alaniz, J. Dysprosium(III) catalysis in organic synthesis. Tetrahedron 2012, 68, 2015-2026.
47. Finke, P.E.; Meurer, L.C.; Levorse, D.A.; Mills, S.G.; MacCoss, M.; Sadowski, S.; Cascieri, M.A.; Tsao, K.-L.; Chicchi, G.G.; Metzger, J.M.; et al. Cyclopentane-based human NK1 antagonists. Part 1: Discovery and initial SAR. Bioorg. Med. Chem. Lett. 2006, 16, 4497-4503.
48. Meurer, L.C.; Finke, P.E.; Owens, K.A.; Tsou, N.N.; Ball, R.G.; Mills, S.G.; MacCoss, M.; Sadowski, S.; Cascieri, M.A.; Tsao, K.-L.; et al. Cyclopentane-based human NK1 antagonists. Part 2: Development of potent, orally active, water-soluble derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 4504-4511.
49. Subba Reddy, B.V.; Narasimhulu, G.; Subba Lakshumma, P.; Vikram Reddy, Y.; Yadav, J.S.; Sridhar, B.; Purushotham Reddy, P.; Kunwar, A.C. Phosphomolybdic acid: A highly efficient solid acid catalyst for the synthesis of trans-4,5-Disubstituted cyclopentenones. Tetrahedron Lett. 2012, 53, 1776-1779.
50. Wenz, D.R.; Read de Alaniz, J. Aza-Piancatelli rearrangement initiated by ring opening of donor-acceptor cyclopropanes. Org. Lett. 2013, 15, 3250-3253.
51. Carson, C.A.; Kerr, M.A. Heterocycles from cyclopropanes: Applications in natural product synthesis. Chem. Soc. Rev. 2009, 38, 3051-3060.
52. Yu, M.; Pagenkopf, B.L. Recent advances in donor-acceptor (DA) cyclopropanes. Tetrahedron 2005, 61, 321-347.
53. Wong, H.N.C.; Hon, M.Y.; Tse, C.W.; Yip, Y.C.; Tanko, J.; Hudlicky, T. Use of cyclopropanes and their derivatives in organic synthesis. Chem. Rev. 1989, 89, 165-198.
54. Palmer, L.I.; Read de Alaniz, J. Direct and highly diastereoselective synthesis of azaspirocycles by a Dysprosium(III) triflate catalyzed aza-piancatelli rearrangement. Angew. Chem. Int. Ed. 2011, 50, 7167-7170.
55. Dake, G. Recent approaches to the construction of 1-Azaspiro[4.5]decanes and related 1-Azaspirocycles. Tetrahedron Lett. 2006, 62, 3467-3492.
56. Burkhard, J.A.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E.M. Synthesis of azaspirocycles and their evaluation in drug discovery. Angew. Chem. Int. Ed. 2010, 49, 3524-3527
57. Palmer, L.I.; Read de Alaniz, J. Rapid and stereoselective synthesis of spirocyclic ethers via the intramolecular piancatelli rearrangement. Org. Lett. 2013, 15, 476-479.
58. Zhang, Q.-W.; Fan, C.-A.; Zhang, H.-J.; Tu, Y.-Q.; Zhao, Y.-M.; Gu, P.; Chen, Z.-M. Brønsted acid catalyzed enantioselective semipinacol rearrangement for the synthesis of chiral spiroethers. Angew. Chem. Int. Ed. 2009, 48, 8572-8574.
59. Adrien, A.; Gais, H.-J.; Köhler, F.; Runsink, J.; Raabe, G. Modular asymmetric synthesis of functionalized azaspirocycles based on the sulfoximine auxiliary. Org. Lett. 2007, 9, 2155-2158.
60. Noguchi, N.; Nakada, M. Synthetic studies on (+)-Ophiobolin α asymmetric synthesis of the spirocyclic CD-Ring moiety. Org. Lett. 2006, 8, 2039-2042.
61. 3-Catalyzed tandem aza-piancatelli rearrangement/michael reaction for the synthesis of 3,4-Dihydro-2H-benzo[b][1,4]thiazine and Oxazine derivatives. RSC Adv. 2012, 2, 10661-10666.
62. Yadav, J.S.; Subba Reddy, B.V.; Hara Gopal, A.V.; Patil, K.S. InBr3-Catalyzed three-component reaction: A facile synthesis of propargyl amines. Tetrahedron Lett. 2009, 50, 3493-3496.
63. 3-Catalyzed synthesis of 4-Thiocyanotetrahydropyrans via a Three-component reaction. Tetrahedron Lett. 2007, 48, 8874-8877
64. 3-Catalyzed cyclization of glycals with aryl amines. Angew. Chem. Int. Ed. 2003, 42, 5198-5201.
65. 3-Promoted a Novel prins cyclization for the synthesis of Hexahydro-1H-furo[3,4-c]pyran derivatives. Tetrahedron Lett. 2012, 53, 2748-2751.
66. Liu, J.; Shen, Q.; Yu, J.; Zhu, M.; Han, J.; Wang, L. A concise domino synthesis of benzo-1,4-heterocycle compounds via a piancatelli/C-N coupling/michael addition process promoted by La(OTf)3. Eur. J. Org. Chem. 2012, 6933-6939.
67. Yin, B.; Huang, L.; Wang, X.; Liu, J.; Jiang, H. Metal-Free rearrangement of spirofurooxindoles into spiropentenoneoxindoles and indoles: Implications for the mechanism and stereochemistry of the piancatelli rearrangement. Adv. Syn. Catal. 2013, 355, 370-376.
68. Yin, B.; Huang, L.; Zhang, X.; Ji, F.; Jiang, H. Cu(II)-Promoted transformations of α-thienylcarbinols into spirothienooxindoles: Regioselective halogenation of dienyl sulfethers containing electron-rich aryl rings. J. Org. Chem. 2012, 77, 6365-6370.
69. Yin, B.-L.; Lai, J.-Q.; Zhang, Z.-R.; Jiang, H.-F. A novel entry to spirofurooxindoles involving tandem dearomatization of furan ring and intramolecular friedel-crafts reaction. Adv. Synth. Catal. 2011, 353, 1961-1965.