Oxidative Amidation of Phenols through the Use of Hypervalent Iodine Reagents: Development and Applications

Abstract

This contribution reviews a family of reactions devised in our laboratory that effect the oxidative conversion of phenols into 4-amido-dienones. A salient feature of this chemistry is the use of hypervalent iodine reagents, especially diacetoxyiodobenzene (DIB), as uniquely capable oxidants in the context of the new transformation. The advent of this methodology has created new opportunities in alkaloid synthesis. Our efforts toward FR-901483, TAN-1251C, cylindricine C, and other nitrogenous natural products illustrate some applications in that domain.

1 Introduction

2 Background

3 First-Generation Oxidative Amidation of Phenols: The Oxazoline Route

4 Initial Applications: Total Synthesis of FR-901483 and of TAN-1251C

5 Second-Generation Oxidative Amidation of Phenols: Sulfonamide Technology

6 Applications: Total Synthesis of (-)-Cylindricine C

7 Third-Generation Solution: The Bimolecular Reaction

8 Conclusion

Key words

phenols - amides - oxidation - hypervalent iodine - alkaloids

References

• 1 Sakamoto K. Tsujii E. Abe F. Nakanishi T. Yamashita M. Shigematsu N. Izumi S. Okuhara M. J. Antibiot.  1996,  49:  37 
• 2 Shirafuji H, Tsubotani S, Ishimaru T, and Harada S. inventors; Int. Patent PCT  WO91/13887. 
• For alternative avenues to these substances, see:
• 3a Snider BB. Lin H. J. Am. Chem. Soc.  1999,  121:  7778 
• 3b Snider BB. Lin H. Org. Lett.  2000,  2:  643 
• 3c Maeng J.-H. Funk RL. Org. Lett.  2001,  3:  1125 
• 3d Kan T. Fujimoto T. Ieda S. Asoh Y. Kitaoka H. Fukuyama T. Org. Lett.  2004,  6:  2729 
• 3e Brummond KM. Hong S. J. Org. Chem.  2005,  70:  907 
• 3f For synthetic studies see: Simila STM. Martin SF. J. Org. Chem.  2007,  72:  5342 ; and references cited therein
• 4 Kikugawa Y. Kawase M. J. Am. Chem. Soc.  1984,  106:  5728 
• 5a Glover SA. Goosen A. McCleland CW. Schoonraad JL. J. Chem. Soc., Perkin Trans. 1  1984,  2255 
• 5b Glover SA. Scott AP. Tetrahedron  1989,  45:  1763 
• 6 Kawase M. Kitamura T. Kikugawa Y. J. Org. Chem.  1989,  54:  3394 
• Reviews:
• 7a Moriarty RM. J. Org. Chem.  2005,  70:  2893 
• 7b Wirth T. Angew. Chem. Int. Ed.  2005,  44:  3656 
• 7c Hamamoto H. Anilkumar G. Tohma H. Kita Y. Chem. Eur. J.  2002,  8:  5377 
• 7d Zhdankin VV. Stang PJ. Chem. Rev.  2002,  102:  2523 
• 7e Moriarty RM. Org. React. (N.Y.)  2001,  57:  327 
• 7f Varvogolis A. Hypervalent Iodine in Organic Synthesis   Academic Press; San Diego CA: 1997. 
• 7g Zhdankin VV. Stang PJ. Chem. Rev.  1996,  96:  1123 
• 8a Kikugawa Y. Kawase M. Chem. Lett.  1990,  581 
• 8b Kikugawa Y. Shimada M. Matsumoto K. Heterocycles  1994,  37:  293 
• 9a Wardrop DJ. Burge MS. J. Org. Chem.  2005,  70:  10271 
• 9b Wardrop DJ. Zhang W. Landrie CL. Tetrahedron Lett.  2004,  45:  4229 
• 9c Wardrop DJ. Burge MS. Chem. Commun.  2004,  1230 
• 9d Wardrop DJ. Landrie CL. Ortiz JA. Synlett  2003,  1352 
• 9e Wardrop DJ. Burge MS. Zhang W. Ortiz JA. Tetrahedron Lett.  2003,  44:  2587 
• 9f Wardrop DJ. Zhang W. Org. Lett.  2001,  3:  2353 
• 9g Wardrop DJ. Basak A. Org. Lett.  2001,  3:  1053 
• 10a Clemente D.-T. Lobo AM. Prabhakar S. Marcelo-Curto MJ. Tetrahedron Lett.  1994,  35:  2043 
• 10b Review: Prata JV. Clemente D.-TS. Prabhakar S. Lobo AM. Mourato I. Branco PS. J. Chem. Soc., Perkin Trans. 1  2002,  513 
• 11 Kikugawa Y. Nagashima A. Sakamoto T. Miyazawa E. Shiiya M. J. Org. Chem.  2003,  68:  6739 
• 12 See, for example: Yamamura S. Chemistry of Phenols   Vol. 2:  Rappoport Z. John Wiley & Sons; Chichester: 2003.  p.1153-1346  
• In particular:
• 13a Usnic acid: Barton DHR. Deflorin AM. Edwards OE. J. Chem. Soc.  1956,  530 
• 13b Galanthamine: Barton DHR. Kirby GW. J. Chem. Soc.  1962,  806 
• 13c For a review, see: Barton DHR. Pure Appl. Chem.  1964,  9:  35 
• Significant contributions by other groups:
• 14a Kametani T. Fukumoto K. Yakugaku Kenkyu  1963,  35:  426 
• 14b Scott AI. McCapra F. Buchanan RL. Day AC. Young DW. Tetrahedron  1965,  21:  3605 
• 15 An excellent survey of the various oxidizing agents that have been employed for the activation of phenols is provided in: Rodríguez S. Wipf P. Synthesis  2004,  2767 
• 16a Tamura Y. Yakura T. Haruta J. Kita Y. J. Org. Chem.  1987,  52:  3927 
• 16b Kita Y. Tohma H. Kikuchi K. Inagaki M. Yakura T. J. Org. Chem.  1991,  56:  435 
• 17 Pelter A. Elgendy S. Tetrahedron Lett.  1988,  29:  677 
• 18 Barret R. Daundon M. Tetrahedron Lett.  1991,  32:  2133 
• 19 Review: Kita Y. Fujioka H. Pure Appl. Chem.  2007,  79:  701 
• 20 Wipf P. Spencer SR. J. Am. Chem. Soc.  2005,  127:  225 
• 21 Wipf P. Jung J.-K. Chem. Rev.  1999,  99:  1469 
• 22a Knapp S. Gibson FS. Org. Synth.  1992,  70:  101 
• 22b Knapp S. In Advances in Heterocyclic Natural Product Synthesis   Vol. 3:  Pearson WH. JAP Press; Greenwich CT: 1996.  Chap. 2.
• Imidates and congeners react at the nitrogen atom with a variety of electrophiles:
• 23a Tennant G.; In Comprehensive Organic Chemistry; Barton D. H. R., Ollis W. D.; Pergamon Press: Oxford, 1979; Vol. 2: Chap. 8, 385-590; see especially page 490 onwards
• 23b Kantlehner W. In Comprehensive Organic Synthesis   Vol. 6:  Trost BM. Pergamon Press; Oxford: 1991.  Chap. 2.7. p.pp 485-599  ; see especially page 529 onwards
• 24a Vorbrüggen H. Krolikiewicz K. Tetrahedron Lett.  1981,  22:  4471 
• 24b Vorbrüggen H. Krolikiewicz K. Tetrahedron  1993,  49:  9353 
• 25 O-Protection of the phenol, by contrast, was essential during assembly of the oxazoline by alternative techniques, such as the Wipf synthesis: Wipf P. Miller CP. Tetrahedron Lett.  1992,  33:  907 
• 26 This stereochemical assignment rests upon X-ray crystallography: Peters K. Peters E.-M. Braun NA. Ciufolini MA. Z. Kristallogr. NCS  1999,  214:  555 
• See:
• 27a Chow YL. Colón CJ. Tan JNS. Can. J. Chem.  1968,  46:  2821 
• 27b Lunazzi L. Cerioni G. Foresti E. Macciantelli D. J. Chem. Soc., Perkin Trans. 2  1980,  717 
• 27c Johnson F. Chem. Rev.  1968,  68:  375 
• 28 Braun NA. Ciufolini MA. Peters K. Peters E.-M. Tetrahedron Lett.  1998,  39:  4667 
• Similar reactions in which a carbonyl group intercepts the electrophilic agent produced upon activation of the phenol are know and are synthetically useful:
• 29a Wong Y.-S. Chem. Commun.  2002,  686 
• 29b Peuchmaur M. Wong Y.-S. J. Org. Chem.  2007,  72:  5374 
• 30 Braun NA. Ousmer M. Bray JD. Bouchu D. Peters K. Peters E.-M. Ciufolini MA. J. Org. Chem.  2000,  65:  4397 
• 31 Dohi T. Morimoto K. Maruyama A. Kita Y. Org. Lett.  2006,  8:  2007 
• 32 Hata K. Hamamoto H. Shiozaki Y. Kita Y. Chem. Commun.  2005,  2465 
• 33 Scheffler G. Seike H. Sorensen EJ. Angew. Chem. Int. Ed.  2000,  39:  4593 
• 34 Mizutani H. Takayama J. Soeda Y. Honda T. Tetrahedron Lett.  2002,  43:  2411 
• 36 Compare with: Aubart KM. Heathcock CH. J. Org. Chem.  1999,  64:  16 
• 38 Review: Tsuda Y. Sano T. The Alkaloids   Vol. 48:  Brossi A. Cordell GA. Academic Press; Orlando: 1996.  p.249 
• 39 Dong Q. Anderson CE. Ciufolini MA. Tetrahedron Lett.  1995,  36:  5681 
• 40 Ousmer M. Braun NA. Bavoux C. Perrin M. Ciufolini MA. J. Am. Chem. Soc.  2001,  123:  7534 
• Two excellent reviews on cylindricines and related compounds have recently appeared:
• 41a Dake G. Tetrahedron  2006,  62:  3467 
• 41b Weinreb SM. Chem. Rev.  2006,  106:  2531 
• 42 See: Ciufolini MA. Hermann CYW. Dong Q. Shimizu T. Swaminathan S. Xi N. Synlett  1998,  105 
• 43 Review: Kan T. Fukuyama T. Chem. Commun.  2004,  353 
• 44a Canesi S. Belmont P. Bouchu D. Rousset L. Ciufolini MA. Tetrahedron Lett.  2002,  43:  5193 
• 44b Canesi S. Bouchu D. Ciufolini MA. Angew. Chem. Int. Ed.  2004,  43:  4336 
• 45 Drutu I. Njardson J. Wood J. Org. Lett.  2002,  4:  493 
• 46a Hutchins RO. Su WY. Sivakumar R. Cistone F. Stercho YP. J. Org. Chem.  1983,  48:  3412 
• 46b Stevens RV. Acc. Chem. Res.  1984,  17:  289 
• 47 Evans DA. Gauchet-Prunet JA. Carreira EM. Charette AB. J. Org. Chem.  1991,  56:  741 ; and references cited therein
• Reviews:
• 48a Gribble GW. Org. Process Res. Dev.  2006,  10:  1062 
• 48b Abdel-Magid AF. Mehrman SJ. Org. Process Res. Dev.  2006,  10:  971 
• 48c Gribble GW. Chem. Soc. Rev.  1998,  27:  395 
• 49 Kita Y. Takada T. Gyoten M. Tohma H. Zenk MH. Eichhorn J. J. Org. Chem.  1996,  61:  5857 
• 50 Canesi S. Bouchu D. Ciufolini MA. Org. Lett.  2005,  7:  175 
• 51 Under these conditions, products arising from capture of the electrophilic intermediate by the azido functionality were not detected; compare with: Kita Y. Egi M. Okajima A. Ohtsubo M. Takada T. Tohma H. Chem. Commun.  1996,  1491 
• 53 Review: Livinghouse T. Tetrahedron  1999,  55:  9947 
• 54 Review: Sinclair A. Stockman RA. Nat. Prod. Rep.  2007,  24:  298 
• In addition to refs. 7, 12, 22, 23, and 40, see:
• 55a Kita Y. Takada T. Gyoten M. Tohma H. Zenk MH. Eichhorn J. J. Org. Chem.  1996,  61:  5854 
• 55b Kita Y. Gyoten M. Ohtsubo M. Tohma H. Takada T. Chem. Commun.  1996,  1481 
• 55c Takada T. Arisawa M. Gyoten M. Hamada R. Tohma H. Kita Y. J. Org. Chem.  1998,  63:  7698 
• 55d Arisawa M. Utsumi S. Nakajima M. Ramesh NG. Tohma H. Kita Y. Chem. Commun.  1999,  469 
• 55e Tohma H. Morioka H. Takizawa S. Arisawa M. Kita Y. Tetrahedron  2001,  345 
• 55f Tohma H. Iwata M. Maegawa T. Kita Y. Tetrahedron Lett.  2002,  43:  9241 
• 55g Dohi T. Morimoto K. Kiyono Y. Maruyama A. Tohma H. Kita Y. Chem. Commun.  2005,  2930 
• 56 Dohi T. Maruyama A. Minamitsuji Y. Takenaga N. Kita Y. Chem. Commun.  2007,  1224 
• 57 Jean A. Cantat J. Berard D. Bouchu D. Canesi S. Org. Lett.  2007,  9:  2553 

35

Canesi, S. unpublished work from these laboratories.

37

Schülé, A. unpublished work from these laboratories.

52

Mendelsohn, B.; Ciufolini, M. A. unpublished work.