Recent applications of the Horner-Wadsworth-Emmons reaction to the synthesis of natural products

Current Organic Chemistry

Volumn 16, Issue 19, 2012, Pages 2206-2230

  Bisceglia, Juan A ^a   Orelli, Liliana R ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Carbonyl olefinations; Horner Wadsworth Emmons (HWE) reaction; Natural products; Stabilized phosphonate carbanions; Total synthesis; , unsaturated carbonyl compounds

Indexed keywords

CARBONYL COMPOUNDS; REACTION INTERMEDIATES; UNSATURATED COMPOUNDS;

CARBONYL OLEFINATION; HORNER-WADSWORTH-EMMONS REACTION; NATURAL PRODUCTS; OLEFINATION; PHOSPHONATES; STABILIZED PHOSPHONATE CARBANION; TOTAL SYNTHESIS; UNSATURATED CARBONYL COMPOUNDS; [CARBONYL; Α,Β-UNSATURATED CARBONYL COMPOUND;

SYNTHESIS (CHEMICAL);

EID: 84870217065     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212803520227     Document Type: Article

References (85)

1. Horner, L.; Hoffmann, H. M. R.; Wippel, H. G. Phosphororganische Verbindungen, XII. Phosphinoxyde als Olefinierungsreagenzien. Ber. 1958, 91, 61-63.
2. Horner, L.; Hoffmann, H. M. R.; Wippel, H. G.; Klahre, G. Phosphororganische Verbindungen, XX. Phosphinoxyde als Olefinierungsreagenzien. Ber. 1959, 92, 2499-2505.
3. Wadsworth W. S, Emmons W. D. The Utility of Phosphonate Carbanions in Olefin Synthesis. J. Am. Chem. Soc. 1961, 83, 1733-1738.
4. Williams, J.M.J. (Ed.) Preparation of Alkenes (Oxford: Oxford University Press, 1996).
5. Trost, B.M.; Fleming, I. (Eds). Comprehensive Organic Synthesis, Vol. 1 (Oxford: Pergamon Press, 1999).
6. Murphy, P.J.; Brennan, J. The Wittig olefination reaction with carbonyl compounds other than aldehydes and ketones. Chem. Soc. Rev. 1988, 17, 1-30.
7. Maryanoff, B.E.; Reitz, A.B. The Wittig Olefination Reaction and Modifications Involving Phosphoryl-Stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects. Chem. Rev. 1989, 89, 863-927.
8. Boutagy, J.; Thomas, R. Olefin Synthesis with Organic Phosphonate Carbanions. Chem. Rev. 1974, 74, 87-99.
9. Korotchenko, V.N.; Nenajdenko, V.G.; Balenkova, E.S.; Shastin, A.V. Elimination of carbonyl compounds: modern and classical methods. Russ. Chem. Rev. 2004, 73 (10), 957-989.
10. Edmonds, M; Abell, A. "The Wittig and related reactions", in Modern Carbonyl Olefination. Takeda, T. (Ed.), 2004, Chapter 1. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
11. Still, W.C.; Gennari, C. Direct synthesis of Z-unsaturated esters. A useful modification of the Horner-Emmons olefination. Tetrahedron Lett. 1983, 24 (41), 4405-4408.
12. Ando, K. Highly Selective Synthesis of Z-Unsaturated Esters by Using New Horner, Emmons Reagents, Ethyl (Diarylphosphono)acetates. J. Org. Chem. 1997, 62, 1934-1939.
13. Ando, K. Z-Selective Horner-Wadsworth-Emmons Reaction of Substituted Ethyl (Diarylphosphono) acetates with Aldehydes. J. Org. Chem. 1998, 63, 8411-8416.
14. Ando, K. Convenient Preparations of (Diphenylphosphono)acetic Acid Esters and the Comparison of the Z-Selectivities of Their Horner-Wadsworth-Emmons Reaction with Aldehydes Depending on the Ester Moiety. J. Org. Chem. 1999, 64, 8406-8408.
15. Ando, K.; Oishi, T.; Hirama, M.; Ibuka, T. Z-Selective Horner-Wadsworth-Emmons Reaction of Ethyl (Diarylphosphono)acetates Using Sodium Iodide and DBU. J. Org. Chem. 2000, 65, 4745-4749.
16. Nicolaou, K.C.; Harter, M.W.; Gunzner, J.L.; Nadin, A. The Wittig and Related Reactions in Natural Product Synthesis, Liebigs Ann./Recueil, 1997, 1283-1301.
17. White, J.D; Lee, T.H; Kuntiyong, P. Total Synthesis of Phorboxazole A. 2. Org. Lett., 2006, 8 (26), 6043-6046.
18. Williams, D.R; Kiryanov, A.A.; Emde, U., Clark, M.P.; Berliner, M.A.; Reeves, J.T. Total Synthesis of Phorboxazole A. Angew. Chem. Int. Ed., 2003, 42 (11), 1258-1262.
19. Li, G.; Yang, X.; Zhai, H. Total Synthesis of (-)-5,6-Dihydrocineromycin B. J. Org. Chem., 2009, 74, 1356-1359.
20. Blanchette, M.A.; Choy, W.; Davis, J.T; Essenfeld, A. P., Masamune, S.; Roush, W.R.; Sakai, T. Horner-Wadsworth-Emmons reaction: Use of lithium chloride and an amine for base-sensitive compounds. Tetrahedron Lett., 1984, 25 (21), 2183-2186.
21. Jiang, X.; Liu, B.; Lebreton, S; De Brabander, J.K. Total Synthesis and Structure Revision of the Marine Metabolite Palmerolide A. J. Am. Chem. Soc., 2007, 129, 6386-6387.
22. Nicolaou, K.C.; Sun, Y.-P.; Guduru, R.; Banerji, B.; Chen, D.Y.-K. Total Synthesis of the Originally Proposed and Revised Structures of Palmerolide A and Isomers Thereof. J. Am. Chem. Soc., 2008, 130, (11) 3633-3644.
23. Suzuki, T.; Usui, K.; Miyake, Y.; Namikoshi, M.; Nakada, M. First Total Synthesis of Antimitotic Compound, (+)-Phomopsidin. Org. Lett., 2004, 6 (4), 553-556.
24. Pirrung, M.C.; Biswas, G.; Ibarra-Rivera, T.R. Total Synthesis of Syringolin A and B. Org. Lett., 2010, 2 (10), 2402-2405.
25. Schauer, D. J.; Helquist, P. Mild Zinc-Promoted Horner-Wadsworth- Emmons Reactions of Diprotic Phosphonate Reagents. Synthesis, 2006, 3654-3660.
26. Müller, S.; Mayer, T.; Sasse, F.; Maier, M.E. Synthesis of a Pladienolide B Analogue with the Fully Functionalized Core Structure. Org. Lett., 2011, 13 (15), 3940-3943.
27. Uenishi, J.; Iwamoto, T.; Tanaka, J. Total Synthesis of (-)-Zampanolide and Questionable Existence of (-)-Dactylolide as the Elusive Biosynthetic Precursor of (-)-Zampanolide in an Okinawan Sponge. Org. Lett., 2009, 11 (15), 3262-3265.
28. Harvey, J.E.; Raw, S.A.; Taylor, R.J.K. The first synthesis of the epoxidecontaining macrolactone nucleus of oximidine I. Tetrahedron Lett., 2003, 44 (38) 7209-7212.
29. Zhong, G.; Yu, Y. Enantioselective Synthesis of Allylic Alcohols by the Sequential Aminoxylation-Olefination Reactions of Aldehydes under Ambient Conditions. Org. Lett. 2004, 6, 1637-1639.
30. Ramulu, U.; Ramesh, D.; Rajaram, S.; Reddy, S.P.; Venkatesham, K.; Venkateswarlu, Y. Stereoselective total synthesis of clonostachydiol. Tetrahedron: Asymmetry, 2012, 23, 117-123.
31. Hong, W.P.; Noshi, M.N.; El-Awa, A.; Fuchs, P.L. Synthesis of the C1C20 and C15C27 Segments of Aplyronine A. Org. Lett., 2011, 13, (24) 6342-6345.
32. Wrona, I.E.; Agouridas, V.; Panek, J.S. Design and synthesis of ansamycin antibiotics. C. R. Chimie, 2008, 11, 1483-1522.
33. Amans, D.; Bellosta, V.; Cossy, J. An Efficient and Stereoselective Synthesis of the Monomeric Counterpart of Marinomycin A. Org. Lett., 2007, 9 (8), 1453-1456.
34. Amans, D.; Bareille, L.; Bellosta, V.; Cossy, J. Synthesis of the Monomeric Counterpart of Marinomycin A. J. Org. Chem., 2009, 74, 7665-7674.
35. Chellat, M.F.; Proust, N.; Lauer, M.G.; Stambuli, J.P. Synthesis of Key Fragments of Leiodelide A. Org. Lett., 2011, 13, (12) 3246-3249.
36. Paterson, I.; Burton, P.M.; Cordier, C.J.; Housden, M.P.; Mühlthau, F.A.; Loiseleur, O. Toward the Total Synthesis of the Brasilinolides: Construction of a Differentially Protected C20-C38. Org. Lett., 2009, 11 (3), 693-696.
37. Nicolaou, K.C.; Li, Y.; Sugita, K.; Monenschein, H.; Guntupalli, P.; Mitchell, H.J.; Fylaktakidou, K.C.; Vourloumis, D.; Giannakakou, P. O'Brate, A. Total Synthesis of Apoptolidin: Completion of the Synthesis and Analogue Synthesis and Evaluation. J. Am. Chem. Soc., 2003, 125, 15443-15454.
38. Roy, S.; Spilling, C.D. Synthesis of the C(18)-C(34) Fragment of Amphidinolide C and the C(18)-C(29) Fragment of Amphidinolide F. Org. Lett., 2010, 12 (22), 5326-5329.
39. Hillier, M.C.; Price, A.T.; Meyers, A. I. Studies on the Total Synthesis of Disorazole C1. An Advanced Macrocycle Intermediate. J. Org. Chem. 2001, 66, 6037-6045.
40. Srinivasarao, M.; Kim, Y.; Li, X.H.; Robbins, D.W.; Fuchs, P.L. Studies on the Synthesis of Apoptolidin: Synthesis of a C1C27 Fragment of Apoptolidin D. J. Org. Chem., 2011, 76, 7834-7841.
41. Li, X.; Lantrip, D.; Fuchs, P.L. γ-Allyl Phosphinoyl Phenyl Sulfone (GAPPS): A Conjunctive Reagent for the Synthesis of EE, EZ, and ET 1,3-Dienes. J. Am. Chem. Soc., 2003, 125 (47) 14262-14263.
42. Ohtani, T.; Kanda, H.; Misawa, K.; Urakawa, Y.; Toshima, K. Synthetic studies of incednine: synthesis of C1-C13 pentaenoic acid segment. Tetrahedron Lett. 2009, 50, 2270-2273.
43. Bentley, D.J.; Slawin, A.M.Z.; Moody, C.J. Total Synthesis of Stephanotic Acid Methyl Ester. Org. Lett., 2006, 8 (10) 1975-1978.
44. Schmidt, U.; Griesser, H.; Leitenberger, V.; Lieberknecht, A.; Mangold, R.; Meyer, R.; Riedl, B. Amino Acids and Peptides. Part 81. Diastereoselective Formation of Z- Didehydroamino Acid Esters. Synthesis, 1992, 487-490.
45. Sánchez, C.C.; Keck, G.E. Total Synthesis of (+)-Dactylolide. Org. Lett., 2005, 7 (14), 3053-3056.
46. Paterson, I.; Yeung, K-S. Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17-C32 subunit of scytophycin C. Tetrahedron Lett., 1993, 34, 5347-5350.
47. Paterson, I.; Yeung, K.-S.; Smaill, J.B. The Horner-Wadsworth-Emmons Reaction in Natural Products Synthesis: Expedient Construction of Complex (E)-Enones Using Barium Hydroxide. Synlett, 1993, 774-776.
48. Jiang, Y.; Hong, J.; Burke, S.D. Stereoselective Total Synthesis of Antitumor Macrolide (+)-Rhizoxin D. Org. Lett., 2004, 6, (9), 1445-1448.
49. Shing, T.K.M.; Cheng, H.M. Short Syntheses of Gabosine I and Gabosine G from d-D-Gluconolactone. J. Org. Chem., 2007, 72, 6610-6613.
50. Yajima, A.; Kagohara, Y.; Shikai, K.; Katsuta, R.; Nukada, T. Synthesis of two osteoclast-forming suppressors, demethylincisterol A3 and chaxine A. Tetrahedron, 2012, 68, 1729-1735.
51. Marco, J.A.; Carda, M.; Murga, J.; Falomir, E. Stereoselective syntheses of naturally occurring 5,6-dihydropyran-2-ones. Tetrahedron, 2007, 63, 2929-2958.
52. Ramana, C.V.; Raghupathi, N.; Gurjar, M.K.; Chorghade, M.S. A carbohydrate-based approach for the total synthesis of strictifolione. Tetrahedron Lett., 2005, 46 (23), 4073-4075.
53. Srihari, P.; Rajendar, G.; Srinivasa Rao, R.; Yadav, J.S. First stereoselective total synthesis of (+)-dodoneine. Tetrahedron Lett., 2008, 49, 5590-5592.
54. Singh, R.P.; Singh, V.K. Facile One-Step Synthesis of b-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group: Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol. J. Org. Chem. 2004, 69, 3425-3430.
55. Yadav, J.S.; Subba Reddy, U.V.; Anusha, B.; Subba Reddy, B. V. The stereoselective total synthesis of (+)-garvensintriol. Tetrahedron Lett., 2010, 51 (42) 5529-5531.
56. Kumar, P.; Pandey, M.; Gupta, P.; Dhavale, D.D. Organocatalytic stereoselective synthesis of passifloricin A. Org. Biomol. Chem., 2012, 10, 1820-1825.
57. Samarat, A.; Landais, Y.; Amri, H. First synthesis of (±)-bishomosarkomycin ethyl ester. Tetrahedron Lett., 2004, 45 (10), 2049-2050.
58. Ghosh, A.K.; Xi, K. Total Synthesis of (-)-Platensimycin, a Novel Antibacterial Agent. J. Org. Chem., 2009, 74, 1163-1170.
59. Kim, M.; Gais, H.-J. Fully Stereocontrolled Syntheses of 3-Oxacarbacyclin and Carbacyclin by the Conjugate Addition-Azoalkene-Asymmetric Olefination Strategy. J. Org. Chem., 2006, 71, 4642-4650.
60. Taillier, C.; Gille, B.; Bellosta, V.; Cossy, J. Synthetic Approaches and Total Synthesis of Natural Zoapatanol. J. Org. Chem., 2005, 70, 2097-2108.
61. J.S. Yu, T.S. Kleckley, D.F. Wiemer. Synthesis of Farnesol Isomers via a Modified Wittig Procedure. Org. Lett. 2005, 7 (22), 4803-4806.
62. Reynaud, E.; Aydemir, G.; Rühl, R.; Dangles, O.; Caris-Veyrat, C. Organic Synthesis of New Putative Lycopene Metabolites and Preliminary Investigation of Their Cell-Signaling Effects. J. Agric. Food Chem. 2011, 59, 1457-1463.
63. Petroski, R.J.; Bartelt, R.J. Direct Aldehyde Homologation Utilized To Construct a Conjugated-Tetraene Hydrocarbon Insect Pheromone. J. Agric. Food Chem., 2007, 55, 2282-2287.
64. Bartelt, R.J.; Weisleder, D.; Plattner, R.D. Synthesis of nitidulid beetle pheromones: alkyl-branched tetraene hydrocarbons. J. Agric. Food Chem., 1990, 38, 2192-2196.
65. Borst, P.; Elferink, R. O. Mammalian ABC transporters in health and disease. Annu. Rev. Biochem. 2002, 71, 537-592.
66. Hohmann, J.; Molnar, J.; Redei, D.; Evanics, F.; Forgo, P.; Kalman, A.; Argay, G.; Szabo, P. Discovery and Biological Evaluation of a New Family of Potent Modulators of Multidrug Resistance: Reversal of Multidrug Resistance of Mouse Lymphoma Cells by New Natural Jatrophane Diterpenoids Isolated from Euphorbia Species. J. Med. Chem. 2002, 45 (12), 2425-2431.
67. Helmboldt, H.; Köhler, D.; Hiersemann, M. Synthesis of the Norjatrophane Diterpene (-)-15-Acetyl-3-propionyl-17-norcharaciol. Org. Lett., 2006, 8 (8), 1573-1576.
68. Odejinmi, S.I.; Wiemer, D.F. Synthesis of arieianal, a prenylated benzoic acid from Piper arieianum. J. Nat. Prod., 2005, 68 (9), 1375-1379.
69. El Fangour, S.; Guy, A.; Despres, V.; Vidal, J.-P.; Rossi, J.-C.; Durand, T. Total Synthesis of the Eight Diastereomers of the Syn-Anti-Syn Phytoprostanes F1 Types I and II. J. Org. Chem., 2004, 69, 2498-2503.
70. Pinot, E.; Guy, A.; Fournial, A.; Balas, L.; Rossi, J.-C.; Durand, T. Total Synthesis of the Four Enantiomerically Pure Diasteroisomers of the Phytoprostanes E1 Type II and of the 15-E2t-Isoprostanes. J. Org. Chem., 2008, 73, 3063-3069.
71. Borbás, A.; Herczegh P. Synthesis of lipid II phosphonate analogues. Carbohydrate Research, 2011, 346 (12) 1628-1632.
72. Modica, E.; Compostella, F.; Colombo, D.; Franchini, L.; Cavallari, M.; Mori, L.; De Libero, G.; Panza, L.; Ronchetti, F. Stereoselective Synthesis and Immunogenic Activity of the C-Analogue of Sulfatide. Org. Lett., 2006, 8 (15), 3255-3258.
73. Lee, H.K Kim, E.-K.; Pak, C.S. Facile transformation of 2-azetidinones to unsaturated ketones: application to the formal synthesis of sphingosine and phytosphingosine. Tetrahedron Lett., 2002, 43 (52), 9641-9644.
74. Jessen, H.J.; Schumacher, A.; Schmid, F.; Pfaltz, A.; Gademann, K. Catalytic Enantioselective Total Synthesis of (+)-Torrubiellone C. Org. Lett., 2011, 13 (16), 4368-4370.
75. Cui, M.; Song, H.; Feng, A.; Wang, Z.; Wang, Q. Asymmetric Synthesis of (R)-Antofine and (R)-Cryptopleurine via Proline-Catalyzed Sequential a- Aminoxylation and Horner-Wadsworth-Emmons Olefination of Aldehyde. J.Org. Chem., 2010, 75, 7018-7021.
76. Reddy, Ch.R.; Latha, B.; Rao, N.N. Enantioselective access to (-)- indolizidines 167B, 209D, 239AB, 195B and (-)-monomorine from a common chiral synthon. Tetrahedron, 2012, 68, 145-151.
77. Shankaraiah, G.; Sateesh Chandra Kumar, R.; Poornima, B.; Suresh Babu, K. Stereoselective synthesis of (+)-radicamine B. Tetrahedron Lett., 2011, 52 (38), 4885-4887.
78. Crimmins, M.T.; Martin, T.J.; Martinot, T.A. Synthesis of the Bistetrahydropyran Core of Amphidinol 3. Org. Lett, 2010, 12 (17), 3890-3893.
79. Fadeyi, O.O.; Lindsley, C.W. Total synthesis of brevisamide. Org. Lett., 2009, 11 (17), 3950-3952.
80. Wilson, Z.E.; Brimble, M.A. A flexible asymmetric synthesis of the tetracyclic core of berkelic acid using a Horner-Wadsworth-Emmons/oxa- Michael cascade. Org. Biomol. Chem., 2010, 8, 1284-1286.
81. Crimmins, M.T; Zuccarello, J.L.; Cleary, P.A.; Parrish, J.D. Convergent, Stereoselective Synthesis of the GHIJ Fragment of Brevetoxin A. Org. Lett., 2006, 8 (1), 159-162.
82. Crimmins, M.T.; McDougall, P.J.; Emmitte, K.A. A Convergent Coupling Strategy for the Formation of Polycyclic Ethers: Stereoselective Synthesis of the BCDE Fragment of Brevetoxin A. Org. Lett., 2005, 7 (18), 4033-4036.
83. Crimmins, M.T.; Shamszad, M.; Mattson, A.E. A Highly Convergent Approach toward (-)-Brevenal. Org. Lett., 2010, 12 (11), 2614-2617.
84. Morita, M.; Ishiyama, S.; Koshino, H.; Nakata, T. Synthetic Studies on Maitotoxin. 1. Stereoselective Synthesis of the C'D'E'F'-Ring System Having a Side Chain. Org. Lett., 2008, 10 (9), 1675-1678.
85. Nicolaou, K.C.; Aversa, R.J.; Jin, J.; Rivas, F. Synthesis of the ABCDEFG Ring System of Maitotoxin. J. Am. Chem.Soc., 2010, 132, 6855-6861.