Bismuth trichloride–mediated cleavage of phenolic methoxymethyl ethers

References

• (a) Young, I. S.; Baran, P. S. Nat. Chem. 2009, 1, 193–205; (b) Huang, B.; Guo, L.; Jia, Y. Angew. Chem., Int. Ed. Engl. 2015, 54, 13599–13603.
   PubMed Web of Science ®Google Scholar
• (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 4th ed.; Wiley & Sons: New York, 1999; (b) Kocienski, P. J. Protecting Group, 3rd ed.; Thieme: New York, 2005.
   Google Scholar
• (a) Auerbach, J.; Weinreb, S. M. J. Chem. Soc., Chem. Commun. 1974, 298–299; (b) Meyers, A. I.; Durandetta, J. L.; Munavu, R. J. Org. Chem. 1975, 40, 2025–2029; (c) Monti, H.; Léandri, G.; Klos-Ringuet, M.; Corriol, C. Synth. Commun. 1983, 13, 1021–1026; (d) Ireland, R. E.; Varney, M. D. J. Org. Chem. 1986, 51, 635–648; (e) Amano, S.; Takemura, N.; Ohtsuka, M.; Ogawa, S.; Chida, N. Tetrahedron 1999, 55, 3855–3870; (f) Boehlow, T. R.; Harburn, J. J.; Spilling, C. D. J. Org. Chem. 2001, 66, 3111–3118; (g) Mander, L. N.; Thomson, R. J. J. Org. Chem. 2005, 70, 1654–1670.
   Google Scholar
• (a) Nakata, T.; Schmid, G.; Vranesic, B.; Okigawa, M.; Smith-Palmer, T.; Kishi, Y. J. Am. Chem. Soc. 1978, 100, 2933–2935; (b) Kieczykowski, G. R.; Schlessinger, R. H. J. Am. Chem. Soc. 1978, 100, 1938–1940; (c) Guindon, Y.; Morton, H. E.; Yoakim, C. Tetrahedron Lett. 1983, 24, 3969–3972; (d) Hanessian, S.; Delorme, D.; Dufresne, Y. Tetrahedron Lett. 1984, 25, 2515–2518; (e) Corey, E. J.; Hua, D. H.; Seitz, S. P. Tetrahedron Lett. 1984, 25, 3–6; (f) Boeckman Jr., R. K.; Potenza, J. C. Tetrahedron Lett. 1985, 26, 1411–1414; (g) Kim, S.; Kee, I. S.; Park, Y. H.; Park, J. H. Synlett 1991, 183–184; (h) Moher, E. D.; Grieco, P. A.; Collins, J. L. J. Org. Chem. 1993, 58, 3789–3790; (i) Paquette, L. A.; Gao, Z.; Ni, Z.; Smith, G. F. Tetrahedron Lett. 1997, 38, 1271–1274; (j) Reddy, S. V.; Rao, R. J.; Kumar, U. S.; Rao, J. M. Chem. Lett. 2003, 32, 1038–1039; (k) Sharma, G. V. M.; Reddy, K. L.; Lakshmi, P. S.; Krishna, P. R. Tetrahedron Lett. 2004, 45, 9229–9232; (l) Yadav, J. S.; Ganganna, B.; Bhunia, D. C.; Srihari, B. P. Tetrahedron Lett. 2009, 50, 4318–4320; (m) Node, M.; Kumar, K.; Nishide, K.; Ohsugi, S.; Miyamoto, T. Tetrahedron Lett. 2001, 42, 9107–9110; (n) Han, J, H.; Kwon, Y. E.; Sohn, J-H.; Ryu, D. H. Tetrahedron 2010, 66, 1673–1677; (o) Ahmed, N.; Pathe, G. K. P.; Babu, V. Tetrahedron Lett. 2014, 55, 3683–3687; (p) Reddy, K. T.; Sreenivasulu, R.; Hatti, I.; Anitha, K.; Raju, R. R. Curr. Org. Synth. 2015, 12, 67–70.
   Web of Science ®Google Scholar
• (a) Deville, J. P.; Behar, V. J. Org. Chem. 2001, 66, 4097–4098; (b) Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Mirjafari, A. Polyhedron 2008, 27, 2612–2624; (c) Ramesh, C.; Ravindranath, N.; Das, B. J. Org. Chem. 2003, 68, 7101–7103.
   PubMed Web of Science ®Google Scholar
• (a) Deville, J. P.; Behar, V. J. Org. Chem. 2001, 66, 4097–4098; (b) Keith, J. M. Tetrahedron Lett. 2004, 45, 2739–2742; (c) Peng, Y.; Ji, C.; Chen, Y.; Huang, C.; Jiang, Y. Synth. Commun. 2004, 34, 4325–4330; (d) Khupse, R. S.; Erhardt, P. W. Org. Lett. 2008, 10, 5007–5010; (e) Fujioka, H.; Kubo, O.; Senami, K.; Minamitsuji, Y.; Maegawa, T. Chem. Commun. 2009, 4429–4431.
   PubMed Web of Science ®Google Scholar
• Sunasee, R.; Clive, D. L. J. J. Org. Chem. 2008, 73, 8016–8020.
   PubMed Web of Science ®Google Scholar
• (a) Briand, G. G.; Burford, N. Chem. Rev. 1999, 99, 2601–2658; (b) Roux, C. L.; Dubac, J. Synlett 2002, 181–200; (c) Leonard, N. M.; Wieland, L. C.; Mohan, R. S. Tetrahedron 2002, 58, 8373–8397; (d) Gaspard-Iloughmane, H.; Le Roux, C. Eur. J. Org. Chem. 2004, 2517–2532; (e) Gaspard-Iloughmane, H.; Le Roux, C. Trends Org. Chem. 2006, 11, 65–80; (f) Hua, R. Curr. Org. Synth. 2008, 5, 1–27; (g) Salvador, J. A. R.; Pinto, R. M. A.; Silvestre, S. M. Curr. Org. Synth. 2009, 6, 426–470; (h) Salvador, J. A. R.; Pinto, R. M. A.; Silvestre, S. M. Mini. Rev. Org. Chem. 2009, 6, 241–274; (i) Bothwell, J. M.; Krabbez, S. W.; Mohan, R. S. Chem. Soc. Rev. 2011, 40, 4649–4707; (j) Ollevier, T. Org. Biomol. Chem. 2013, 11, 2740–2755.
   PubMed Web of Science ®Google Scholar
• Salvador, J. A. R.; Figueiredo, S. A. C.; Pinto, R. M. A.; Silvestre, S. M. Future Med. Chem. 2012, 4, 1495–1523.
   PubMed Web of Science ®Google Scholar
• Sreedhar, B.; Swapna, V.; Sridhar, C. Catal. Commun. 2005, 6, 293–296.
   Web of Science ®Google Scholar
• A comparative cost of bismuth trichloride (25 g = $83) versus bismuth trifluoromethanesulphonate (25 g = $273) from Sigma Aldrich source.
   Google Scholar
• (a) McDougal, N. T.; Schaus, S. E. J. Am. Chem. Soc. 2003, 125, 12094–12095; (b) Wang, H. Chirality 2010, 22, 827–837.
   PubMed Web of Science ®Google Scholar
• Kigoshi, H.; Adachi, Y.; Yoshikawa, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 4195–4198.
   Web of Science ®Google Scholar
• Vannada, J.; Bennett, E. M.; Wilson, D. J.; Boshoff, H. I.; Barry, C. E. 3rd.; Aldrich, C. C. Org. Lett. 2006, 8, 4707–4710.
   PubMed Web of Science ®Google Scholar