Subscribe to RSS
DOI: 10.1055/s-0033-1338650
The Glycol Cleavage in Natural Product Synthesis: Reagent Classics and Recent Advances
Publication History
Received: 06 March 2014
Accepted after revision: 07 March 2014
Publication Date:
17 November 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201424/lookinside/thumbnails/10.1055-s-0033-1338650-1.jpg)
Abstract
This review focuses on the application of glycol cleavage reactions in the synthesis and derivatization of complex natural products. Reagent classics as well as recent developments are discussed.
1 Introduction
2 Mechanistic Aspects
3 Reagents and Examples
3.1 Periodate and Hypervalent Iodine
3.1.1 Periodic Acid and Periodates
3.1.2 Periodate on Wet Silica Gel
3.1.3 Phenyliodine Diacetate
3.1.4 Other Iodine Reagents
3.2 Lead Tetraacetate
3.3 Chromium Reagents
3.3.1 Pyridinium Chlorochromate
3.3.2 Other Chromium Reagents
3.4 Ruthenium Reagents
3.4.1 Tetra-n-propylammonium Perruthenate
3.4.2 Other Ruthenium Reagents
3.5 Manganese Reagents
3.5.1 Manganese(III) Acetate
3.5.2 Manganese Dioxide
3.5.3 Other Manganese Reagents
3.6 Miscellaneous
4 Conclusion
-
References
- 1a Malaprade L. Bull. Soc. Chim. Fr. 1928; 43: 683
- 1b Malaprade L. C. R. Hebd. Seances Acad. Sci. 1928; 186: 382
- 2 Criegee R. Ber. Dtsch. Chem. Ges. B 1931; 64: 260
- 3a Shing TK. M In Comprehensive Organic Synthesis . Vol. 7. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 703
- 3b Perlin AS. Adv. Carbohydr. Chem. Biochem. 2006; 60: 183
- 4 Buist GJ, Bunton CA, Hipperson WC. P. J. Chem. Soc. B 1971; 2128
- 5 Price CC, Knell M. J. Am. Chem. Soc. 1942; 64: 552
- 6 Criegee R, Höger E, Huber G, Kruck P, Marktscheffel F, Schellenberger H. Justus Liebigs Ann. Chem. 1956; 599: 81
- 7 For reviews, see: Ermolinsky BS, Mikhailov SN. Bioorg. Khim. 2000; 26: 483 . See also: references 1–3
- 8 Nicolaou KC, Zhong Y.-L, Baran PS, Jung J, Choi H.-S, Yoon WH. J. Am. Chem. Soc. 2002; 124: 2202
- 9 Ohyabu N, Nishikawa T, Isobe M. J. Am. Chem. Soc. 2003; 125: 8798
- 10a Gao S, Wang Q, Chen C. J. Am. Chem. Soc. 2009; 131: 1410
- 10b Gao S, Wang Q, Huang LJ.-S, Lum L, Chen C. J. Am. Chem. Soc. 2010; 132: 371
- 11a Teruya T, Nakagawa S, Koyama T, Arimoto H, Kita M, Uemura D. Tetrahedron 2004; 60: 6989
- 11b Teruya T, Nakagawa S, Koyama T, Suenaga K, Kita M, Uemura D. Tetrahedron Lett. 2003; 44: 5171
- 12 Keck GE, Poudel YB, Cummins TJ, Rudra A, Covel JA. J. Am. Chem. Soc. 2011; 133: 744
- 13 Huang A, Kodanko JJ, Overman LE. J. Am. Chem. Soc. 2004; 126: 14043
- 14 Zhang H, Sridhar Reddy M, Phoenix S, Deslongchamps P. Angew. Chem. Int. Ed. 2008; 47: 1272
- 15 Williams DR, Werner KM, Feng B. Tetrahedron Lett. 1997; 38: 6825
- 16 Jiang Y, Hong J, Burke SD. Org. Lett. 2004; 6: 1445
- 17 Keck GE, Park M, Krishnamurthy D. J. Org. Chem. 1993; 58: 3787
- 18 Winkler JD, Quinn KJ, MacKinnon CH, Hiscock SD, McLaughlin EC. Org. Lett. 2003; 5: 1805
- 19a Schöttner E, Wiechoczek M, Jones PG, Lindel T. Org. Lett. 2010; 12: 784
- 19b Simon K, Wefer J, Schöttner E, Lindel T. Angew. Chem. Int. Ed. 2012; 51: 10889
- 20 Lee TW, Corey EJ. J. Am. Chem. Soc. 2001; 123: 1872
- 21 Zakarian A, Batch A, Holton RA. J. Am. Chem. Soc. 2003; 125: 7822
- 22 Tanuwidjaja J, Ng S.-S, Jamison TF. J. Am. Chem. Soc. 2009; 131: 12084
- 23a Chan J, Jamison TF. J. Am. Chem. Soc. 2003; 125: 11514
- 23b Chan J, Jamison TF. J. Am. Chem. Soc. 2004; 126: 10682
- 24 Trost BM, Dong G, Vance JA. J. Am. Chem. Soc. 2007; 129: 4540
- 25 Smith AB. III, Bosanac T, Basu K. J. Am. Chem. Soc. 2009; 131: 2348
- 26a Funahashi Y, Kawamura N, Ishimaru T. JP 08231551 [A2960910], 1996 ; Chem. Abstr. 1996, 126, 6553
- 26b Funahashi N, Kawamura N. JP 08231552, 1996 ; Chem. Abstr. 1996, 126, 326518
- 26c Su MH, Hosken MI, Hotovec BJ, Johnston TL. US Patent 5728727, 1998 ; Chem. Abstr. 1998, 128, 239489
- 26d Bode HB, Zeeck AJ. J. Chem. Soc., Perkin Trans. 1 2000; 323
- 26e Bode HB, Zeeck AJ. J. Chem. Soc., Perkin Trans. 1 2000; 2665
- 26f Martin HJ, Magauer T, Mulzer J. Angew. Chem. Int. Ed. 2010; 49: 5614
- 27 Mulzer J, Pichlmair S, Green MP, Marques MM. B, Martin HJ. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 11980
- 28 Yen C.-F, Liao C.-C. Angew. Chem. Int. Ed. 2002; 41: 4090
- 29a Igarashi M, Nakagawa N, Doi S, Hattori N, Naganawa H, Hamada M. J. Antibiot. 2003; 56: 580
- 29b Takeuchi T, Igarashi M, Naganawa H. JP P2003-12687A, 2003
- 30 Hirano S, Ichikawa S, Matsuda A. Angew. Chem. Int. Ed. 2005; 44: 1854
- 31 Yang J, Wu H, Shen L, Qin Y. J. Am. Chem. Soc. 2007; 129: 13794
- 32 Lerchner A, Carreira EM. J. Am. Chem. Soc. 2002; 124: 14826
- 33a Trost BM, Gunzner JL. J. Am. Chem. Soc. 2001; 123: 9449
- 33b Trost BM, Dirat O, Gunzner JL. Angew. Chem. Int. Ed. 2002; 41: 841
- 33c Trost BM, Gunzner JL, Dirat O, Rhee YH. J. Am. Chem. Soc. 2002; 124: 10396
-
34a Dai M, Krauss IJ, Danishefsky SJ. J. Org. Chem. 2008; 73: 9576
-
34b Dai MJ, Danishefsky SJ. J. Am. Chem. Soc. 2007; 129: 3498
- 35 Ge HM, Zhang L.-D, Tan RX, Yao Z.-J. J. Am. Chem. Soc. 2012; 134: 12323
- 36a Galindev O, Badraa N, Dalantai M, Sengee G.-I, Dorjnamjin D, Shim YK. Photochem. Photobiol. Sci. 2008; 7: 1273
- 36b Wang J, Zhao Y, Yin J, Wu X. Huaxue Tongbao 2002; 65: 782
- 36c McCarthy JR, Hyland MA, Brückner C. Org. Biomol. Chem. 2004; 2: 1484
- 36d Ryppa C, Niedzwiedzki D, Morozowich NL, Srikanth R, Zeller M, Frank HA, Brückner C. Chem. Eur. J. 2009; 15: 5749
- 36e Akhigbe J, Ryppa C, Zeller M, Brückner C. J. Org. Chem. 2009; 74: 4927
- 37 Wang T, Xu Q, Yu P, Liu X, Cook JM. Org. Lett. 2001; 3: 345
- 38 Ishikawa H, Elliott GI, Velcicky J, Choi Y, Boger DL. J. Am. Chem. Soc. 2006; 128: 10596
- 39 Inoue M, Miyazaki K, Uehara H, Maruyama M, Hirama M. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 12013
- 40 Gallimore AR, Spencer JB. Angew. Chem. Int. Ed. 2006; 45: 4406
- 41 Li G, Yang X, Zhai H. J. Org. Chem. 2009; 74: 1356
- 42 Chen Z.-H, Chen Z.-M, Zhang Y.-Q, Tu Y.-Q, Zhang F.-M. J. Org. Chem. 2011; 76: 10173
- 43 Giroux S, Corey EJ. Org. Lett. 2008; 10: 801
- 44a Zhong Y, Shing TK. M. J. Org. Chem. 1997; 62: 2622
- 44b Baptista FS. Res. J. Chem. Environ. 2007; 11: 78
- 44c Rezaeivala M. Synlett 2006; 3550
- 44d Bhalay G, Dunstan A, Glen A. Synlett 2000; 1846
- 44e Ley SV, Baxendale IR, Bream RN, Jackson PS, Leach AG, Longbottom DA, Nesi M, Scott JS, Storer RI, Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000; 1472
- 44f Drewry DH, Coe DM, Poon S. Med. Res. Rev. 1999; 19: 97
- 45a Gupta DN, Hodge P, Davies JE. J. Chem. Soc., Perkin Trans. 1 1981; 2970
- 45b Daumas M, Vo-Quang Y, Vo-Quang L, Gaffic FL. Synthesis 1989; 64
- 46a Paquette LA, Peng X, Bondar D. Org. Lett. 2002; 4: 937
- 46b Peng X, Bondar D, Paquette LA. Tetrahedron 2004; 60: 9589
- 47a Saito T, Fuwa H, Sasaki M. Org. Lett. 2009; 11: 5274
- 47b Saito T, Fuwa H, Sasaki M. Tetrahedron 2011; 67: 429
- 48 Panarese JD, Waters SP. Org. Lett. 2009; 11: 5086
- 49 Spangler JE, Sorensen EJ. Tetrahedron 2009; 65: 6739
- 50 Baird MC, Pyne SG, Ung AT, Lie W, Sastraruji T, Jatisatienr A, Jatisatienr C, Dheeranupattana S, Lowlam J, Boonchalermkit S. J. Nat. Prod. 2009; 72: 679
- 51 García-Fortanet J, Murga J, Carda M, Marco JA, Matesanz R, Díaz JF, Barasoain I. Chem. Eur. J. 2007; 13: 5060
- 52 Personal communication.
- 53 Mejorado LH, Pettus TR. R. J. Am. Chem. Soc. 2006; 128: 15625
- 54 Mejorado L, Pettus TR. R. Synthesis 2006; 3209
- 55a Liao X, Xu X. Tetrahedron Lett. 2000; 41: 4641
- 55b Liu P, Liao X.-B, Xu X.-X. Chin. J. Chem. 2003; 21: 811
- 56 Su J, Long K, Pang T, Zeng L, Zheng Q, Lin X. Sci. Sin., Ser. B 1988; 31: 1172
- 57 Kinsman AC, Kerr MA. Org. Lett. 2001; 3: 3189
- 58 Kinsman AC, Kerr MA. J. Am. Chem. Soc. 2003; 125: 14120
- 59 Piccialli V. Synthesis 2007; 2585
- 60 Brown RC. D, Bataille CJ, Hughes RM, Kenney A, Luker TJ. J. Org. Chem. 2002; 67: 8079
- 61 Liu Z.-y, Yu C.-z, Wang R.-F, Li G. Tetrahedron Lett. 1998; 39: 5261
- 62 Liu Z.-Y, Chen Z.-C, Yu C.-Z, Wang R.-F, Zhang R.-Z, Huang C.-S, Yan Z, Cao D.-R, Sun J.-B, Li G. Chem. Eur. J. 2002; 8: 3747
- 63 Liao X, Wu Y, De Brabander JK. Angew. Chem. Int. Ed. 2003; 42: 1648
- 64 Mushti CS, Kim J.-H, Corey EJ. J. Am. Chem. Soc. 2006; 128: 14050
- 65 Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 66 Sharefkin JG, Saltzman H. Org. Synth. 1963; 43: 62
- 67 Criegee R, Beucker H. Justus Liebigs Ann. Chem. 1939; 541: 218
- 68 Nicolaou KC, Adsool VA, Hale CR. H. Org. Lett. 2010; 12: 1552
- 69 Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. J. Org. Chem. 1996; 61: 3849
- 70a Okawara M, Mizuta K. Kogyo Kagaku Zasshi 1961; 64: 232
- 70b Yamada Y, Okawara M. Makromol. Chem. 1972; 152: 153
- 70c Chen F.-E, Xie B, Zhang P, Zhao J.-F, Wang H, Zhao L. Synlett 2007; 619
- 71 Malik G, Guinchard X, Crich D. Org. Lett. 2012; 14: 596
- 72 Shibuya M, Shibuta T, Fukuda H, Iwabuchi Y. Org. Lett. 2012; 14: 5010
- 73a Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 73b Dess DB, Martin JC. J. Am. Chem. Soc. 1991; 113: 7277
- 73c Grieco PA, Collins JL, Moher ED, Fleck TJ, Gross RS. J. Am. Chem. Soc. 1993; 115: 6078
- 73d VanderRoest JM, Grieco PA. J. Am. Chem. Soc. 1993; 115: 5841
- 73e Pancrazi A, Anies C, Collemand J. Tetrahedron Lett. 1995; 36: 7771
- 74 De Munari S, Frigerio M, Santagostino M. J. Org. Chem. 1996; 61: 9272
- 75 Moorthy JN, Singhal N, Senapati K. Org. Biomol. Chem. 2007; 5: 767
- 76a Criegee R In Oxidation in Organic Chemistry . Wiberg K. Academic Press; New York: 1965. Part A
- 76b Rubottom GM. Organic Chemistry . In Oxidation in Organic Chemistry . Vol. 5; Trahanovsky WS. Academic Press; New York: 1982. Part D, 1-145
- 77 Rawlinson DJ, Sosnovsky G. Synthesis 1973; 567
- 78 Criegee R, Kraft L, Rank B. Justus Liebigs Ann. Chem. 1933; 507: 159
- 79 Criegee R, Büchner E. Ber. Dtsch. Chem. Ges. B 1940; 73: 563
- 80 Wender PA, Jankowski OD, Tabet EA, Seto H. Org. Lett. 2003; 5: 2299
- 81 Baer E. J. Am. Chem. Soc. 1940; 62: 1597
- 82 Hirata Y, Nakamura S, Watanabe N, Kataoka O, Kurosaki T, Anada M, Kitagaki S, Shiro M, Hashimoto S. Chem. Eur. J. 2006; 12: 8898
- 83a Arseniyadis S, Yashunsky DV, Toupet L, Wang Q, Potier P. Tetrahedron Lett. 1995; 36: 8783
- 83b Arseniyadis S, Yashunsky DV, Perreira de Freitas R, Muños Dorado M, Potier P, Toupet L. Tetrahedron 1996; 52: 12443
- 84 Unaleroglu C, Aviyente V, Arseniyadis S. J. Org. Chem. 2002; 67: 2447
- 85a Candela Lena JI, Martín Hernando JI, del Rosario Rico Ferreira M, Altinel E, Arseniyadis S. Synlett 2001; 597
- 85b Candela Lena JI, Rico Ferreira MR, Martín Hernando JI, Altinel E, Arseniyadis S. Tetrahedron Lett. 2001; 42: 3179
- 85c Candela Lena JI, Altinel E, Birlirakis N, Arseniyadis S. Tetrahedron Lett. 2002; 43: 1409
- 85d Lena JI. C, Fernandez EM. S, Ramani A, Birlirakis N, Barrero AF. A. F, Arseniyadis S. Eur. J. Org. Chem. 2005; 683
- 86 Candela Lena JI, Sesenoglu Ö, Birlirakis N, Arseniyadis S. Tetrahedron Lett. 2001; 42: 21
- 87 Snaddon TN, Buchgraber P, Schulthoff S, Wirtz C, Mynott R, Fürstner A. Chem. Eur. J. 2010; 16: 12133
- 88 Mehta G, Pan SC. Org. Lett. 2004; 6: 3985
- 89 Schwartz KD, White JD. Org. Lett. 2011; 13: 248
- 90 Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
- 91a Li P, Li J, Arikan F, Ahlbrecht W, Dieckmann M, Menche D. J. Org. Chem. 2010; 75: 2429
- 91b Li P, Li J, Arikan F, Ahlbrecht W, Dieckmann M, Menche D. J. Am. Chem. Soc. 2009; 131: 11678
- 92a Mehta G, Singh V. Chem. Rev. 1999; 99: 881
- 92b Ferraz H, Bombonato F, Longo LJr. Synthesis 2007; 3261
- 92c Kleinke AS, Webb D, Jamison TF. Tetrahedron 2012; 68: 6999
- 93 Lee TV, Porter JR, Roden FS. Tetrahedron 1991; 47: 139
- 94a Méndez-Andino J, Paquette LA. Org. Lett. 2000; 2: 1263
- 94b Balskus EP, Méndez-Andino J, Arbit RM, Paquette LA. J. Org. Chem. 2001; 66: 6695
- 95a Inoue M, Sato T, Hirama M. Angew. Chem. Int. Ed. 2006; 45: 4843
- 95b Inoue M, Sato T, Hirama M. J. Am. Chem. Soc. 2003; 125: 10772
- 95c Inoue M, Lee N, Kasuya S, Sato T, Hirama M, Moriyama M, Fukuyama Y. J. Org. Chem. 2007; 72: 3065
- 96 Liu P, Panek JS. J. Am. Chem. Soc. 2000; 122: 1235
- 97 Fettes A, Carreira EM. Angew. Chem. Int. Ed. 2002; 41: 4098
- 98 Rychnovsky SD, Swenson SS. J. Org. Chem. 1997; 62: 1333
- 99 Kadota I, Hu Y, Packard GK, Rychnovsky SD. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 11992
- 100a Ondeyka JG, Helms GL, Hensens OD, Goetz MA, Zink DL, Tsipouras A, Shoop WL, Slayton L, Dombrowski AW, Polishook JD, Ostlind DA, Tsou NN, Ball RG, Singh SB. J. Am. Chem. Soc. 1997; 119: 8809
- 100b Hensens OD, Ondeyka JG, Dombrowski AW, Ostlind DA, Zink DL. Tetrahedron Lett. 1999; 40: 5455
- 101 Chakravarty PK, Tyagarajan S, Shih TL, Salva S, Snedden C, Wyvratt MJ, Fisher MH, Meinke PT. Org. Lett. 2002; 4: 1291
- 102 Corey EJ, Xiang YB. Tetrahedron Lett. 1988; 29: 995
- 103 Kogure N, Ishii N, Kitajima M, Wongseripipatana S, Takayama H. Org. Lett. 2006; 8: 3085
- 104 Carter KD, Panek JS. Org. Lett. 2004; 6: 55
- 105 Deka V, Dubois J, Thoret S, Guéritte F, Guénard D. Org. Lett. 2003; 5: 5031
- 106 Sun C, Lin X, Weinreb SM. J. Org. Chem. 2006; 71: 3159
- 107 Paterson I, Chen D, Coster M. Angew. Chem. Int. Ed. 2001; 40: 4055
- 108 Cowden CJ, Paterson I. Org. React. 1997; 51: 1
- 109 Cisneros A, Fernández S, Hernández JE. Synth. Commun. 1982; 12: 833
- 110 Li J.-T, Liu X.-R, Liu X.-F. Ultrason. Sonochem. 2009; 16: 4
- 111a Chang YW, Westheimer FW. J. Am. Chem. Soc. 1960; 82: 1401
- 111b Kwart H, Ford JA. Jr, Corey GC. J. Am. Chem. Soc. 1962; 84: 1252
- 112a Ruthenium in Organic Synthesis . Murahashi S.-I. Wiley-VCH; Weinheim: 2004
- 112b Ruthenium Catalysts in Fine Chemistry . In Topics in Organometallic Chemistry . Vol. 11. Bruneau C, Dixneuf PH. Springer; Berlin, Heidelberg: 2004
- 113 Plietker B. Synthesis 2005; 2453
- 114 Griffith WP, Ley SV, Whitcombe GP, White AD. J. Chem. Soc., Chem. Commun. 1987; 1625
- 115a Griffith WP, Ley SV. Aldrichimica Acta 1990; 23: 13
- 115b Ley SV, Norman J, Griffith WP, Marsden SP. Synthesis 1994; 639
- 115c Langer P. J. Prakt. Chem. 2000; 342: 728
- 116 Schmidt A.-KC, Stark CB. W. Org. Lett. 2011; 13: 4164
- 117 Acosta CK, Rao PN, Kim HK. Steroids 1993; 58: 205
- 118 Wiberg KB, Snoonian JR. J. Org. Chem. 1998; 63: 1402
- 119 Schmidt A.-KC, Stark CB. W. Org. Lett. 2011; 13: 5788
- 120a Hartung IV, Hoffmann HM. R. Angew. Chem. Int. Ed. 2004; 43: 1934
- 120b Hoffmann HM. R, Dunkel R, Mentzel M, Reuter H, Stark CB. W. Chem. Eur. J. 2001; 7: 4771
- 121 Hashimoto N, Aoyama T, Shioiri T. Chem. Pharm. Bull. 1981; 29: 1475
- 122 Takezawa E, Sakaguchi S, Ishii Y. Org. Lett. 1999; 1: 715
- 123a Fatiadi AJ. Synthesis 1976; 56
- 123b Fatiadi AJ. Synthesis 1976; 133
- 123c Fatiadi AJ. Synthesis 1987; 85
- 124a Candela Lena JI, Martín Hernando JI, del Rosario Rico Ferreira M, Altinel E, Arseniyadis S. Synlett 2001; 597
- 124b Grieco PA, Collins JL, Moher ED, Fleck TJ, Gross RS. J. Am. Chem. Soc. 1993; 115: 6078
- 125 Ohloff G, Giersch W. Angew. Chem., Int. Ed. Engl. 1973; 12: 401
- 126 Outram HS, Raw SA, Taylor RJ. K. Tetrahedron Lett. 2002; 43: 6185
- 127 Taylor RJ. K, Reid M, Foot J, Raw SA. Acc. Chem. Res. 2005; 38: 851
- 128 Riaño S, Fernández D, Fadini L. Catal. Commun. 2008; 9: 1282
- 129 Barroso S, Blay G, Fernández I, Pedro JR, Ruiz-García R, Pardo E, Lloret F, Muñoz MC. J. Mol. Catal. A: Chem. 2006; 243: 214
- 130 Rigby W. J. Chem. Soc. 1950; 1907
- 131a Barton DH. R, Finet J.-P, Motherwell WB, Pichon C. Tetrahedron 1986; 42: 5627
- 131b Postel M, Duñach E. Coord. Chem. Rev. 1996; 155: 127
- 132a Greenspan FP, Woodburn HM. J. Am. Chem. Soc. 1954; 76: 6345
- 132b Kumar A. J. Am. Chem. Soc. 1981; 103: 5179
- 133a Nakagawa K, Konaka R, Nakata T. J. Org. Chem. 1962; 27: 1597
- 133b Konaka R, Kuruma K. J. Org. Chem. 1971; 36: 1703
- 134 McKillop A, Raphael RA, Taylor EC. J. Org. Chem. 1972; 37: 4204
- 135a De Vries G, Schors A. Tetrahedron Lett. 1968; 9
- 135b Morimoto T, Hirano M. J. Chem. Soc., Perkin Trans. 2 1982; 1087
- 135c Mastrorilli P, Suranna G, Nobile CG J. Mol. Catal. A 2000; 156: 279
- 135d Iwahama T, Yoshino Y, Keitoku T, Sakaguchi S, Ishii Y. J. Org. Chem. 2000; 65: 6502
- 136a Venturello C, Ricci M. J. Org. Chem. 1986; 51: 1599
- 136b Shimizu M, Orita H, Suzuki K, Hayakawa T, Hamakawa S, Takehira K. J. Mol. Catal. A: Chem. 1996; 114: 217
- 137 Kaneda K, Morimoto K, Imanaka T. Chem. Lett. 1988; 1295
- 138a Littler JS. J, Waters WA. W. A, Mallet AI. J. Chem. Soc. 1960; 2767
- 138b Kirihara M, Yoshida K, Noguchi T, Naito S, Matsumoto N, Ema Y, Torii M, Ishizuka Y, Souta I. Tetrahedron Lett. 2010; 51: 3619
- 139a Okamoto T, Sasaki K, Oka S. J. Am. Chem. Soc. 1988; 110: 1187
- 139b Ito Y, Kunimoto K, Miyachi S, Kako T. Tetrahedron Lett. 1991; 32: 4007
- 140 Shibuya M, Doi R, Shibuta T, Uesugi S, Iwabuchi Y. Org. Lett. 2012; 14: 5006
- 141 Zhao MZ, Li J, Mano E, Song ZG, Tschaen DM, Grabowski EJ. J, Reider PJ. J. Org. Chem. 1999; 64: 2564
For a review, see:
For related glycol cleavages of the tetrapyrrole core, see:
For reviews, see:
It should be noted that there were previous reports on silica gel supported periodate but such reagents appear not to be as practical as the reagent described in ref. 44a; see:
For related work, see:
For reviews, see:
For an early result on the Dess–Martin periodinane mediated cleavage of vicinal diols, see: