10.1002/anie.201803887
Angewandte Chemie International Edition
COMMUNICATION
[1]
Selected review articles: a) B. H. Novak, T. Hudlicky, J. W. Reed, J.
Mulzer, D. Trauner, Curr. Org. Chem. 2000, 4, 343-362; b) T. Hudlicky,
Can. J. Chem. 2015, 93, 492-501; c) B. Sandor, C. Csaba, S. Attila, Curr.
Med. Chem. 2009, 16, 3215-3242; d) B. Murphy, I. Šnajdr, A. Machara,
M. A. A. Endoma-Arias, T. C. Stamatatos, D. P. Cox, T. Hudlický, Adv.
Synth. Catal. 2014, 356, 2679-2687; e) J. W. Reed, T. Hudlicky, Acc.
Chem. Res. 2015, 48, 674-687; f) U. Rinner, T. Hudlicky, in Alkaloid
Synthesis (Ed.: H.-J. Knölker), Springer Berlin Heidelberg, Berlin,
Heidelberg, 2012, pp. 33-66; g) J. Zezula, T. Hudlicky, Synlett 2005,
2005, 388-405; h) P. R. Blakemore, J. D. White, Chem. Commun.
(Cambridge, U. K.) 2002, 1159-1168; Selected syntheses of thebaine,
codeine, morphine or derivatives: i) M. Gates, G. Tschudi, J. Am. Chem.
Soc. 1952, 74, 1109-1110; j) M. Gates, G. Tschudi, J. Am. Chem. Soc.
1956, 78, 1380-1393; k) R. Grewe, W. Friedrichsen, Chem. Ber. 1967,
100, 1550-1558; l) M. A. Schwartz, I. S. Mami, J. Am. Chem. Soc. 1975,
97, 1239-1240; m) K. C. Rice, J. Org. Chem. 1980, 45, 3135-3137; n) M.
A. Schwartz, M. F. Zoda, J. Org. Chem. 1981, 46, 4623-4625; o) J. D.
White, G. Caravatti, T. B. Kline, E. Edstrom, K. C. Rice, A. Brossi,
Tetrahedron 1983, 39, 2393-2397; p) D. G. Vanderlaan, M. A. Schwartz,
J. Org. Chem. 1985, 50, 743-747; q) M. A. Schwartz, K. Pham Phuong
Thi, J. Org. Chem. 1988, 53, 2318-2322; r) M. A. Tius, M. A. Kerr, J. Am.
Chem. Soc. 1992, 114, 5959-5966; s) J. Mulzer, J. W. Bats, B. List, T.
Opatz, D. Trauner, Synlett 1997, 441-444; t) B. M. Trost, W. Tang, J. Am.
Chem. Soc. 2002, 124, 14542-14543; u) G. Stork, A. Yamashita, J.
Adams, G. R. Schulte, R. Chesworth, Y. Miyazaki, J. J. Farmer, J. Am.
Chem. Soc. 2009, 131, 11402-11406; v) T. Erhard, G. Ehrlich, P. Metz,
Angew. Chem. Int. Ed. 2011, 50, 3892-3894; Angew. Chem. 2011, 123,
3979-3981; w) V. Varghese, T. Hudlicky, Angew. Chem. Int. Ed. 2014,
53, 4355-4358; Angew. Chem. 2014, 126, 4444-4447; x) M. Tissot, R. J.
Phipps, C. Lucas, R. M. Leon, R. D. M. Pace, T. Ngouansavanh, M. J.
Gaunt, Angew. Chem. Int. Ed. 2014, 53, 13498–13501; Angew. Chem.
2014, 126, 13716–13719; y) M. Geffe, T. Opatz, Org. Lett. 2014, 16,
5282-5285; z) S. Chu, N. Münster, T. Balan, M. D. Smith, Angew. Chem.,
Int. Ed. 2016, 55, 14306-14309; Angew. Chem. 2016, 128, 14518-14521;
aa) H. Umihara, S. Yokoshima, M. Inoue, T. Fukuyama, Chem. Eur. J.
2017, 23, 6993-6995; ab) P. Koukal, J. Hájíček, S. Gupta, T. Hudlický,
ChemistrySelect 2017, 2, 7783-7786; ac) J. Rautschek, A. Jäger, P. Metz,
Org. Lett. 2018, 20, 832-835.
[4]
[5]
[6]
a) D. H. R. Barton, D. S. Bhakuni, R. James, G. W. Kirby, J. Chem. Soc.
C 1967, 128-132; b) D. H. R. Barton, G. W. Kirby, W. Steglich, G. M.
Thomas, Proceedings of the Chemical Society 1963, 189-228.
a) C. Szántay, G. Blaskó, M. Bárczai-Beke, P. Péchy, G. Dörnyei,
Tetrahedron Lett. 1980, 21, 3509-3512; b) H. Hamamoto, Y. Shiozaki, H.
Nambu, K. Hata, H. Tohma, Y. Kita, Chem. Eur. J. 2004, 10, 4977-4982.
a) K. D. Moeller, Chem. Rev. 2018; b) M. Yan, Y. Kawamata, P. S. Baran,
Chem. Rev. 2017, 117, 13230-13319; c) Y. Jiang, K. Xu, C. Zeng, Chem.
Rev. 2017; d) J.-i. Yoshida, A. Shimizu, R. Hayashi, Chem. Rev. 2017;
e) R. Francke, R. D. Little, Chem. Soc. Rev. 2014, 43, 2492-2521; f) S.
Möhle, M. Zirbes, E. Rodrigo, T. Gieshoff, A. Wiebe, S. R. Waldvogel,
Angew. Chem. Int. Ed. 2018, 57, 6018-6041; Angew. Chem. 2018, 130,
6124-6149; g) A. Wiebe, T. Gieshoff, S. Möhle, E. Rodrigo, M. Zirbes, S.
R. Waldvogel, Angew. Chem. Int. Ed. 2018, 57, 5594-5619; Angew.
Chem. 2018, 130, 5694-5721; h) M. Atobe, H. Tateno, Y. Matsumura,
Chem. Rev. 2018, 118, 4541-4572.
L. L. Miller, F. R. Stermitz, J. R. Falck, J. Am. Chem. Soc. 1971, 93, 5941-
5942. The anodic coupling of reticuline derivatives was investigated by
Bobbitt et al., but the yields (≈ 15%) were much lower than those obtained
with laudanosine derivatives: J. M. Bobbitt, I. Noguchi, R. S. Ware, K. N.
Chiong, S. J. Huang, J. Org. Chem. 1975, 40, 2924-2928.
a) L. L. Miller, F. R. Stermitz, J. R. Falck, J. Am. Chem. Soc. 1973, 95,
2651-2656; b) L. L. Miller, R. F. Stewart, J. P. Gillespie, V.
Ramachandran, Y. H. So, F. R. Stermitz, J. Org. Chem. 1978, 43, 1580-
1586; c) A. Brockmeyer, PhD-thesis, Westfälische Wilhelms-Universität
Münster (Münster), 2003; d) H. Klünenberg, C. Schäffer, H.-J. Schäfer,
Tetrahedron Lett. 1982, 23, 4581-4584; e) E. Kotani, S. Tobinaga,
Tetrahedron Lett. 1973, 14, 4759-4762; f) T. W. Bentley, S. J. Morris, J.
Org. Chem. 1986, 51, 5005-5007.
[7]
[8]
[9]
a) J. R. Falck, L. L. Miller, F. R. Stermitz, Tetrahedron 1974, 30, 931-934;
b) H. Klünenberg, PhD-thesis, Westfälische Wilhelms-Universität
Münster (Münster), 1981.
[10] M. Geffe, PhD-thesis, Johannes Gutenberg-Universität Mainz (Mainz),
2016.
[11] a) J. M. Bobbitt, R. C. Hallcher, J. Chem. Soc. D: Chem. Commun. 1971,
543-544; b) B. Lipp, A. Lipp, H. Detert, T. Opatz, Org. Lett. 2017, 19,
2054-2057.
[12] a) L. L. Miller, F. R. Stermitz, J. Y. Becker, V. Ramachandran, J. Am.
Chem. Soc. 1975, 97, 2922-2923; b) J. Y. Becker, L. L. Miller, F. R.
Stermitz, J. Electroanal. Chem. 1976, 68, 181-191; c) J. B. Kerr, T. C.
Jempty, L. Miller, J. Am. Chem. Soc. 1979, 101, 7338-7346; d) L.
Christensen, L. L. Miller, J. Org. Chem. 1981, 46, 4876-4880.
[13] D. Stubba, G. Lahm, M. Geffe, J. W. Runyon, A. J. Arduengo III, T. Opatz,
Angew. Chem. Int. Ed. 2015, 54, 14187-14189; Angew. Chem. 2015, 127,
14394-14396.
[14] a) F. Werner, N. Blank, T. Opatz, Eur. J. Org. Chem. 2007, 3911-3915;
b) J. C. Liermann, T. Opatz, J. Org. Chem. 2008, 73, 4526-4531; c) N.
Blank, T. Opatz, J. Org. Chem. 2011, 76, 9777-9784; d) N. Otto, D.
Ferenc, T. Opatz, J. Org. Chem. 2017, 82, 1205-1217.
[2]
[3]
a) G. W. Kirby, Science 1967, 155, 170-173; b) D. H. R. Barton, T. Cohen,
Festschrift A. Stoll, Birkhäuser Basle, 1957.
a) T. Kametani, K. Fukumoto, Synthesis 1972, 657-674; b) T. Kametani,
K. Fukumoto, F. Satoh, Bioorg. Chem. 1974, 3, 430-497; c) K. L. Stuart,
Chem. Rev. 1971, 71, 47-72; d) W. W.-C. Chan, P. Maitland, J. Chem.
Soc. C 1966, 753-757; e) A. H. Jackson, J. A. Martin, J. Chem. Soc. C
1966, 2061-2069; f) B. Franck, G. Dunkelmann, H. J. Lubs, Angew.
Chem. Int. Ed. 1967, 6, 1075-1076; Angew. Chem. 1967, 79, 1066-1067;
g) T. Kametani, K. Fukumoto, A. Kozuka, H. Yagi, M. Koizumi, J. Chem.
Soc. C 1969, 2034-2036; h) T. Kametani, A. Kozuka, K. Fukumoto, J.
Chem. Soc. C 1971, 1021-1024; i) M. A. Schwartz, Synth. Commun.
1973, 3, 33-35; j) M. P. Cava, K. T. Buck, Tetrahedron 1969, 25, 2795-
2805; k) T. Kametani, T. Sugahara, H. Yagi, K. Fukumoto, Tetrahedron
1969, 25, 3667-3673; l) G. Blasko, G. Dornyei, M. Barczai-Beke, P.
Pechy, C. Szantay, J. Org. Chem. 1984, 49, 1439-1441.
[15] a) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem.
Soc. 1996, 118, 4916-4917; b) G. J. Meuzelaar, M. C. A. van Vliet, L.
Maat, R. A. Sheldon, Eur. J. Org. Chem. 1999, 2315-2321.
This article is protected by copyright. All rights reserved.