Download PDF
Banert, K. et al.: 2019 Science of Synthesis: Knowledge Updates 2018/4 DOI: 10.1055/sos-SD-137-00001
Knowledge Updates 2018/4

37.3 Oxetanes and Oxetan-3-ones

More Information

Book

Editors: Banert, K.; Clarke, P. A.; Drabowicz, J.; Oestreich, M.

Authors: Benoit, E.; Bull, J. A.; Croft, R. A.; Gagnon, A.; Kawęcki, R.; Kleoff, M.; Le Roch, A.; Omoregbee, K.; Podlech, J.; Zimmer, R.

Title: Knowledge Updates 2018/4

Print ISBN: 9783132423251; Online ISBN: 9783132423282; Book DOI: 10.1055/b-006-161209

1st edition © 2019 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Type: Multivolume Edition

Also available at
 

Abstract

This is a completely revised chapter on the synthesis of oxetanes and oxetan-3-ones, covering the literature up to early 2018. The last 10 years has seen many new approaches to the synthesis of oxetanes, prompted by increased interest in the use of oxetane derivatives in medicinal chemistry. Developments include cyclization methods for ring formation, as well as functionalization of oxetane-containing building blocks.

Key words

oxetanes - oxetanones - oxygen heterocycles - cyclization - Williamson ether synthesis - Paternò–Büchi photocycloaddition - carbon-oxygen bonds - four-membered rings - carbon-oxygen bond formation - carbon-carbon bond formation
 
  • 1 Bull J. A, Croft R. A, Davis O. A, Doran R, Morgan K. F. Chem. Rev 2016; 116: 12 150
  • 2 Burkhard J. A, Wuitschik G, Rogers-Evans M, Müller K, Carreira E. M. Angew. Chem. Int. Ed 2010; 49: 9052
  • 3 Pell A. S, Pilcher G. Trans. Faraday Soc 1965; 61: 71
  • 4 Eigenmann H. K, Golden D. M, Benson S. W. J. Phys. Chem 1973; 77: 1687
  • 5 Malapit C. A, Howell A. R. J. Org. Chem 2015; 80: 8489
  • 6 Wang Z, Chen Z, Sun J. Org. Biomol. Chem 2014; 12: 6028
  • 7 Kudo H, Nishikubo T. J. Polym. Sci., Part A: Polym. Chem 2007; 45: 709
  • 8 Darensbourg D. J, Horn Jr. A, Moncada A. I. Green Chem 2010; 12: 1376
  • 9 Wuitschik G, Carreira E. M, Wagner B, Fischer H, Parrilla I, Schuler F, Rogers-Evans M, Müller K. J. Med. Chem 2010; 53: 3227
  • 10 McLaughlin M, Yazaki R, Fessard T. C, Carreira E. M. Org. Lett 2014; 16: 4070
  • 11 Powell N. H, Clarkson G. J, Notman R, Raubo P, Martin N. G, Shipman M. Chem. Commun. (Cambridge) 2014; 50: 8797
  • 12 Möller G. P, Müller S, Wolfstädter B. T, Wolfrum S, Schepmann D, Wünsch B, Carreira E. M. Org. Lett 2017; 19: 2510
  • 13 Croft R. A, Mousseau J. J, Choi C, Bull J. A. Chem.–Eur. J 2016; 22: 16 271
  • 14 Lassalas P, Oukoloff K, Makani V, James M, Tran V, Yao Y, Huang L, Vijayendran K, Monti L, Trojanowski J. Q, Lee V. M.-Y, Kozlowski M. C, Smith III A. B, Brunden K. R, Ballatore C. ACS Med. Chem. Lett 2017; 8: 864
  • 15 Croft R. A, Mousseau J. J, Choi C, Bull J. A. Chem.–Eur. J 2018; 24: 818
  • 16 Stepan A. F, Karki K, McDonald W. S, Dorff P. H, Dutra J. K, DiRico K. J, Won A, Subramanyam C, Efremov I. V, O’Donnell C. J, Nolan C. E, Becker S. L, Pustilnik L. R, Sneed B, Sun H, Lu Y, Robshaw A. E, Riddell D, O’Sullivan T. J, Sibley E, Capetta S, Atchison K, Hallgren A. J, Miller E, Wood A, Obach R. S. J. Med. Chem 2011; 54: 7772
  • 17 Searles S, Gortatowski M. J. J. Am. Chem. Soc 1953; 75: 3030
  • 18 Searles S, Nickerson R. G, Witsiepe W. K. J. Org. Chem 1959; 24: 1839
  • 19 Reboul M. Ann. Chim. (Paris) 1878; 14: 495
  • 20 Wender P. A, Badham N. F, Conway S. P, Floreancig P. E, Glass T. E, Houze J. B, Krauss N. E, Lee D, Marquess D. G, McGrane P. L, Meng W, Natchus M. G, Shuker A. J, Sutton J. C, Taylor R. E. J. Am. Chem. Soc 1997; 119: 2757
  • 21 Morihira K, Hara R, Kawahara S, Nishimori T, Nakamura N, Kusama H, Kuwajima I. J. Am. Chem. Soc 1998; 120: 12 980
  • 22 Soai K, Niwa S, Yarnanoi T, Hikima H, Ishizaki M. J. Chem. Soc., Chem. Commun 1986; 1018
  • 23 Lo M. M.-C, Fu G. C. Tetrahedron 2001; 57: 2621
  • 24 Aftab T, Carter C, Hart J, Nelson A. Tetrahedron Lett 1999; 40: 8679
  • 25 Aftab T, Carter C, Christlieb M, Hart J, Nelson A. J. Chem. Soc., Perkin Trans. 1 2000; 711
  • 26 Roy B. G, Roy A, Achari B, Mandal S. B. Tetrahedron Lett 2006; 47: 7783
  • 27 Kawahata Y, Takatsuto S, Ikekawa N, Murata M, Omura S. Chem. Pharm. Bull 1986; 34: 3102
  • 28 Nishiyama S, Yamamura S, Kato K, Takita T. Tetrahedron Lett 1988; 29: 4743
  • 29 Nicolaou K. C, Yang Z, Liu J. J, Ueno H, Nantermet P. G, Guy R. K, Claiborne C. F, Renaud J, Couladouros E. A, Paulvannan K. Nature (London) 1994; 367: 630
  • 30 Danishefsky S. J, Masters J. J, Young W. B, Link J. T, Snyder L. B, Magee T. V, Jung D. K, Isaacs R. C. A, Bornmann W. G, Alaimo C. A, Coburn C. A, Di Grandi M. J. J. Am. Chem. Soc 1996; 118: 2843
  • 31 Holton R. A, Kim H.-B, Somoza C, Liang F, Biediger R. J, Boatman P. D, Shindo M, Smith C. C, Kim S, Nadizadeh H, Suzuki Y, Tao C, Vu P, Tang S, Zhang P, Murthi K. K, Gentile L. N, Liu J. H. J. Am. Chem. Soc 1994; 116: 1599
  • 32 Doi T, Fuse S, Miyamoto S, Nakai K, Sasuga D, Takahashi T. Chem.–Asian J 2006; 1: 370
  • 33 Fukaya K, Kodama K, Tanaka Y, Yamazaki H, Sugai T, Yamaguchi Y, Watanabe A, Oishi T, Sato T, Chida N. Org. Lett 2015; 17: 2574
  • 34 Boyd S, Davies C. D. Tetrahedron Lett 2014; 55: 4117
  • 35 Behrendt J. M, Bala K, Golding P, Hailes H. C. Tetrahedron Lett 2005; 46: 643
  • 36 Dussault P. H, Trullinger T. K, Noor-e-Ain F. Org. Lett 2002; 4: 4591
  • 37 Guo Y.-A, Lee W, Krische M. J. Chem.–Eur. J 2017; 23: 2557
  • 38 Davies A. T, Slawin A. M. Z, Smith A. D. Chem.–Eur. J 2015; 21: 18 944
  • 39 Sevrin M, Krief A. Tetrahedron Lett 1980; 21: 585
  • 40 Okuma K, Tanaka Y, Kaji S, Ohta H. J. Org. Chem 1983; 48: 5133
  • 41 Fitton A. O, Hill J, Jane D. E, Millar R. Synthesis 1987; 1140
  • 42 Welch S. C, Prakasa Rao A. S. C. J. Am. Chem. Soc 1979; 101: 6135
  • 43 Welch S. C, Prakasa Rao A. S. C, Lyon J. T, Assercq J. M. J. Am. Chem. Soc 1983; 105: 252
  • 44 Butova E. D, Barabash A. V, Petrova A. A, Kleiner C. M, Schreiner P. R, Fokin A. A. J. Org. Chem 2010; 75: 6229
  • 45 Sone T, Lu G, Matsunaga S, Shibasaki M. Angew. Chem. Int. Ed 2009; 48: 1677
  • 46 Austin G. N, Fleet G. W. J, Peach J. M, Prout K, Son J. C. Tetrahedron Lett 1987; 28: 4741
  • 47 Johnson S. W, Angus D, Taillefumier C, Jones J. H, Watkin D. J, Floyd E, Buchanan J. G, Fleet G. W. J. Tetrahedron: Asymmetry 2000; 11: 4113
  • 48 Barker S. F, Angus D, Taillefumier C, Probert M. R, Watkin D. J, Watterson M. P, Claridge T. D. W, Hungerford N. L, Fleet G. W. J. Tetrahedron Lett 2001; 42: 4247
  • 49 Witty D. R, Fleet G. W. J, Vogt K, Wilson F. X, Wang Y, Storer R, Myers P. L, Wallis C. J. Tetrahedron Lett 1990; 31: 4787
  • 50 Witty D. R, Fleet G. W. J, Choi S, Yogt K, Wilson F. X, Wang Y, Storer R, Myers P. L, Wallis C. J. Tetrahedron Lett 1990; 31: 6927
  • 51 Saksena A. K, Ganguly A. K, Girijavallabhan V. M, Pike R. E, Chen Y.-T, Puar M. S. Tetrahedron Lett 1992; 33: 7721
  • 52 Fleet G. W. J, Son J. C, Peach J. M, Hamor T. A. Tetrahedron Lett 1988; 29: 1449
  • 53 Fleet G. W. J, Son J. C, Vogt K, Peach J. M, Hamor T. A. Tetrahedron Lett 1988; 29: 1451
  • 54 Homsi F, Rousseau G. J. Org. Chem 1999; 64: 81
  • 55 Albert S, Robin S, Rousseau G. Tetrahedron Lett 2001; 42: 2477
  • 56 Evans R. D, Magee J. W, Schauble J. H. Synthesis 1988; 862
  • 57 Jung M. E, Nichols C. J. Tetrahedron Lett 1996; 37: 7667
  • 58 Galatsis P, Millan S. D, Ferguson G. J. Org. Chem 1997; 62: 5048
  • 59 Rofoo M, Roux M.-C, Rousseau G. Tetrahedron Lett 2001; 42: 2481
  • 60 Arjona O, Fernndez de la Pradilla R, Plumet J, Viso A. Tetrahedron 1989; 45: 4565
  • 61 Arjona O, Fernndez de la Pradilla R, Plumet J, Viso A. J. Org. Chem 1992; 57: 772
  • 62 Willand-Charnley R, Puffer B. W, Dussault P. H. J. Am. Chem. Soc 2014; 136: 5821
  • 63 Still W. C. Tetrahedron Lett 1976; 2115
  • 64 Mordini A, Bindi S, Pecchi S, Degl’Innocenti A, Reginato G, Serci A. J. Org. Chem 1996; 61: 4374
  • 65 Mordini A, Bindi S, Pecchi S, Capperucci A, Degl’Innocenti A, Reginato G. J. Org. Chem 1996; 61: 4466
  • 66 Mordini A, Bindi S, Capperucci A, Nistri D, Reginato G, Valacchi M. J. Org. Chem 2001; 66: 3201
  • 67 Williams D. R, Grote J. J. Org. Chem 1983; 48: 134
  • 68 Bird C. W, Hormozi N. Tetrahedron Lett 1990; 31: 3501
  • 69 Mordini A, Valacchi M, Nardi C, Bindi S, Poli G, Reginato G. J. Org. Chem 1997; 62: 8557
  • 70 Morgan K. F, Hollingsworth I. A, Bull J. A. Chem. Commun. (Cambridge) 2014; 50: 5203
  • 71 Morgan K. F, Hollingsworth I. A, Bull J. A. Org. Biomol. Chem 2015; 13: 5265
  • 72 Morgan K. F, Doran R, Croft R. A, Hollingsworth I. A, Bull J. A. Synlett 2016; 27: 106
  • 73 Davis O. A, Bull J. A. Angew. Chem. Int. Ed 2014; 53: 14 230
  • 74 Davis O. A, Croft R. A, Bull J. A. Chem. Commun. (Cambridge) 2015; 51: 15 446
  • 75 Davis O. A, Bull J. A. Synlett 2015; 26: 1283
  • 76 D’Auria M, Racioppi R. Molecules 2013; 18: 11 384
  • 77 Wang Z. Comprehensive Organic Named Reactions and Reagents. Wiley; Hoboken, NJ 2010. 2126.
    Google Scholar
  • 78 Fréneau M, Hoffmann N. J. Photochem. Photobiol., C 2017; 33: 83
  • 79 Abe M. J. Chin. Chem. Soc. (Taipei) 2008; 55: 479
  • 80 Fukuyama T, Kajihara Y, Hino Y, Ryu I. J. Flow Chem 2011; 1: 40
  • 81 Terao K, Nishiyama Y, Kakiuchi K. J. Flow Chem 2014; 4: 35
  • 82 Stinson C. A, Xia Y. Analyst 2016; 141: 3696
  • 83 Bach T. Tetrahedron Lett 1991; 32: 7037
  • 84 Vogt F, Jödicke K, Schröder J, Bach T. Synthesis 2009; 4268
  • 85 Bach T. Tetrahedron Lett 1994; 35: 5845
  • 86 Bach T. Angew. Chem. Int. Ed 1996; 35: 884
  • 87 Bach T, Schröder J. J. Org. Chem 1999; 64: 1265
  • 88 Bach T, Schröder J. Synthesis 2001; 1117
  • 89 Griesbeck A. G, Stadtmüller S. J. Am. Chem. Soc 1991; 113: 6923
  • 90 Griesbeck A. G, Stadtmüller S. J. Am. Chem. Soc 1990; 112: 1281
  • 91 Griesbeck A. G, Fiege M, Lex J. Chem. Commun. (Cambridge) 2000; 589
  • 92 Adam W, Peters K, Peters E. M, Stegmann V. R. J. Am. Chem. Soc 2000; 122: 2958
  • 93 Adam W, Stegmann V. R. Synthesis 2001; 1203
  • 94 Griesbeck A. G, Bondock S. J. Am. Chem. Soc 2001; 123: 6191
  • 95 Rivas C, Vélez M, Crescente O. J. Chem. Soc., Chem. Commun 1970; 1474
  • 96 Rivas C, Bolívar R. A, Cucarella M. J. Heterocycl. Chem 1982; 19: 529
  • 97 Nakano T, Rodríguez W, de Roche S. Z, Larrauri J. M, Rivas C, Pérez C. J. Heterocycl. Chem 1980; 17: 1777
  • 98 Bach T, Bergmann H, Brummerhop H, Lewis W, Harms K. Chem.–Eur. J 2001; 7: 4512
  • 99 Khan N, Morris T. H, Smith E. H, Walsh R. J. Chem. Soc., Perkin Trans. 1 1991; 865
  • 100 D’Auria M, Emanuele L, Racioppi R. Tetrahedron Lett 2004; 45: 3877
  • 101 Hu S, Neckers D. C. J. Org. Chem 1997; 62: 564
  • 102 Hu S, Neckers D. C. J. Org. Chem 1996; 61: 6407
  • 103 Iriondo-Alberdi J, Perea-Buceta J. E, Greaney M. F. Org. Lett 2005; 7: 3969
  • 104 Hammaecher C, Portella C. Chem. Commun. (Cambridge) 2008; 5833
  • 105 Sakamoto M, Takahashi M, Fujita T, Watanabe S, Nishio T, Iida I, Aoyama H. J. Org. Chem 1997; 62: 6298
  • 106 Wang Z, Chen Z, Sun J. Angew. Chem. Int. Ed 2013; 52: 6685
  • 107 Wojtowicz J. A, Polak R. J. J. Org. Chem 1973; 38: 2061
  • 108 Wang Y, Fleet G. W. J, Wilson F. X, Storer R, Wallis C. J, Doherty O, Watkin D. J, Vogt K, Witty D. R, Peach J. M. Tetrahedron Lett 1991; 32: 1675
  • 109 Sakya S. M, Strohmeyer T. W, Bitha P, Lang Jr. S. A, Lin Y.-I. Bioorg. Med. Chem. Lett 1997; 7: 1805
  • 110 Estrada A. A, Chan B. K, Baker-Glenn C, Beresford A, Burdick D. J, Chambers M, Chen H, Dominguez S. L, Dotson J, Drummond J, Flagella M, Fuji R, Gill A, Halladay J, Harris S. F, Heffron T. P, Kleinheinz T, Lee D. W, Le Pichon C. E, Liu X, Lyssikatos J. P, Medhurst A. D, Moffat J. G, Nash K, Scearce-Levie K, Sheng Z, Shore D. G, Wong S, Zhang S, Zhang X, Zhu H, Sweeney Z. K. J. Med. Chem 2014; 57: 921
  • 111 Wuitschik G, Rogers-Evans M, Müller K, Fischer H, Wagner B, Schuler F, Polonchuk L, Carreira E. M. Angew. Chem. Int. Ed 2006; 45: 7736
  • 112 Wuitschik G. 2008
  • 113 Billen S, Curtis M, Ewin R. A, Goodwin R. M, Johnson P. D, Johnson T. A, Kyne G. M, Maddux T. M, Sheehan S. M. K, Vairagoundar R. US 2014 088 046, 2014
  • 114 Heimann A, Dahmann G, Grundl M, Mueller S. G, Wellenzohn B. WO 2013 087 805, 2013
  • 115 Boyer S, Härter M, Wickens P, Patel M, Kumarasinghe E. S, Bhargava A. K, Thierauch K.-H, Beck H, Greschat S, Ellinghaus P, Paulus P, Hess-Stumpp H. WO 2008 141 731, 2008
  • 116 Aversa R. J, Burger M. T, Dillon M. P, Dineen Jr. T. A, Lou Y, Nishiguchi G. A, Ramurthy S, Rico A. C, Rauniyar V, Sendzik M, Subramanian S, Setti L. Q, Taft B. R, Tanner H. R, Wan L. WO 2016 038 582, 2016
  • 117 Lucas S. D, Rauter A. P, Schneider J, Wessel H. P. J. Carbohydr. Chem 2009; 28: 431
  • 118 Chordia M. D, Chaudary A. G, Kingston D. G. I, Jiang Y. Q, Hamel E. Tetrahedron Lett 1994; 35: 6843
  • 119 Aliagas-Martin I, Crawford J, Lee W, Mathieu S, Rudolph J. WO 2013 026 914, 2013
  • 120 Zahler R. WO 2016 112 088, 2016
  • 121 Bowers S, Truong A. P, Ye M, Aubele D. L, Sealy J. M, Neitz R. J, Hom R. K, Chan W, Dappen M. S, Galemmo Jr. R. A, Konradi A. W, Sham H. L, Zhu Y. L, Beroza P, Tonn G, Zhang H, Hoffman J, Motter R, Fauss D, Tanaka P, Bova M. P, Ren Z, Tam D, Ruslim L, Baker J, Pandya D, Diep L, Fitzgerald K, Artis D. R, Anderson J. P, Bergeron M. Bioorg. Med. Chem. Lett 2013; 23: 2743
  • 122 Estrada A. A, Shore D. G, Blackwood E, Chen Y.-H, Deshmukh G, Ding X, DiPasquale A. G, Epler J. A, Friedman L. S, Koehler M. F. T, Liu L, Malek S, Nonomiya J, Ortwine D. F, Pei Z, Sideris S, St-Jean F, Trinh L, Truong T, Lyssikatos J. P. J. Med. Chem 2013; 56: 3090
  • 123 Kinoshita K, Kobayashi T, Asoh K, Furuichi N, Ito T, Kawada H, Hara S, Ohwada J, Hattori K, Miyagi T, Hong W.-S, Park M.-J, Takanashi K, Tsukaguchi T, Sakamoto H, Tsukuda T, Oikawa N. J. Med. Chem 2011; 54: 6286
  • 124 Kinoshita K, Ono Y, Emura T, Asoh K, Furuichi N, Ito T, Kawada H, Tanaka S, Morikami K, Tsukaguchi T, Sakamoto H, Tsukuda T, Oikawa N. Bioorg. Med. Chem. Lett 2011; 21: 3788
  • 125 Phillips D. P, Gao W, Yang Y, Zhang G, Lerario I. K, Lau T. L, Jiang J, Wang X, Nguyen D. G, Bhat B. G, Trotter C, Sullivan H, Welzel G, Landry J, Chen Y, Joseph S. B, Li C, Gordon W. P, Richmond W, Johnson K, Bretz A, Bursulaya B, Pan S, McNamara P, Seidel H. M. J. Med. Chem 2014; 57: 3263
  • 126 Song Z, Yang Y, Liu Z, Peng X, Guo J, Yang X, Wu K, Ai J, Ding J, Geng M, Zhang A. J. Med. Chem 2015; 58: 197
  • 127 Hamzik P. J, Brubaker J. D. Org. Lett 2010; 12: 1116
  • 128 Jung H. H, Buesking A. W, Ellman J. A. Org. Lett 2011; 13: 3912
  • 129 Brady P. B, Carreira E. M. Org. Lett 2015; 17: 3350
  • 130 Phelan J. P, Ellman J. A. Adv. Synth. Catal 2016; 358: 1713
  • 131 Wuitschik G, Rogers-Evans M, Buckl A, Bernasconi M, Märki M, Godel T, Fischer H, Wagner B, Parrilla I, Schuler F, Schneider J, Alker A, Schweizer W. B, Müller K, Carreira E. M. Angew. Chem. Int. Ed 2008; 47: 4512
  • 132 Beadle J. D, Knuhtsen A, Hoose A, Raubo P, Jamieson A. G, Shipman M. Org. Lett 2017; 19: 3303
  • 133 Phelan J. P, Patel E. J, Ellman J. A. Angew. Chem. Int. Ed 2014; 53: 11 329
  • 134 Monleón A, Glaus F, Vergura S, Jørgensen K. A. Angew. Chem. Int. Ed 2016; 55: 2478
  • 135 Duncton M. A. J, Estiarte M. A, Tan D, Kaub C, O’Mahony D. J. R, Johnson R. J, Cox M, Edwards W. T, Wan M, Kincaid J, Kelly M. G. Org. Lett 2008; 10: 3259
  • 136 Bhonde V. R, O’Neill B. T, Buchwald S. L. Angew. Chem. Int. Ed 2016; 55: 1849
  • 137 Molander G. A, Traister K. M, O’Neill B. T. J. Org. Chem 2014; 79: 5771
  • 138 Duncton M. A. J, Estiarte M. A, Johnson R. J, Cox M, O’Mahony D. J. R, Edwards W. T, Kelly M. G. J. Org. Chem 2009; 74: 6354
  • 139 Ravelli D, Zoccolillo M, Mella M, Fagnoni M. Adv. Synth. Catal 2014; 356: 2781
  • 140 Jin J, MacMillan D. W. C. Angew. Chem. Int. Ed 2015; 54: 1565
  • 141 Malapit C. A, Chitale S. M, Thakur M. S, Taboada R, Howell A. R. J. Org. Chem 2015; 80: 5196
  • 142 Ndakala A. J, Howell A. R. J. Org. Chem 1998; 63: 6098
  • 143 Howell A. R, Ndakala A. J. Org. Lett 1999; 1: 825
  • 144 Dollinger L. M, Howell A. R. J. Org. Chem 1996; 61: 7248
  • 145 Rowland A. T, Bennett P. J, Shoupe T. S. J. Org. Chem 1968; 33: 2426
  • 146 Pons M, Simons Jr. S. S. J. Org. Chem 1981; 46: 3262
  • 147 Kozikowski A. P, Fauq A. H. Synlett 1991; 783
  • 148 Thijs L, Cillissen P. J. M, Zwanenburg B. Tetrahedron 1992; 48: 9985
  • 149 Geden J. V, Beasley B. O, Clarkson G. J, Shipman M. J. Org. Chem 2013; 78: 12 243
  • 150 Ye L, He W, Zhang L. J. Am. Chem. Soc 2010; 132: 8550
  • 151 Maegawa T, Otake K, Hirosawa K, Goto A, Fujioka H. Org. Lett 2012; 14: 4798