An efficient synthesis of functionalized helicenes

Journal of the American Chemical Society

Volumn 119, Issue 42, 1997, Pages 10054-10063

  Katz, Thomas J ^a   Liu, Longbin ^a   Willmore, Nikolaos D ^a   Fox, Joseph M ^a   Rheingold, Arnold L ^b   Shi, Shuhao ^a   Nuckolls, Colin ^a   Rickman, Barry H ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; QUINONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0030721577     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9721327     Document Type: Article

References (117)

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11. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
12. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
13. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
14. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
15. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
16. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
17. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
18. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
19. See footnote 12 in ref 7b. In addition, stilbene cyclizations: (a) Staab; H. A.; Diehm, M.; Krieger, C. Tetrahedron Lett. 1994, 35, 8357. (b) Larsen, J.; Bechgaard, K. J. Org. Chem. 1996, 67, 1151. (c) Laatsch, H.; Talvitie, A.; Kral, A.; Ernst, B.-P.; Noltemeyer, M. J. Prakt. Chem. 1996, 338, 140. Biaryl couplings: (d) Tanaka, K.; Suzuki, H.; Osuga, H. J. Org. Chem. 1997, 62, 4465, and references therein, (e) Pereira, D. E.; Neelima; Leonard, N. J. Tetrahedron 1990, 46, 5895. (f) Pischel, I.; Grimme, S.; Kotila, S.; Nieger, M.; Vögtle, F. Tetrahedron Asymmetry 1996, 7, 109. The trimerization of 9,10-dichlorophenanthrene: (g) Carey, J. G.; Millar, I. T. J. Chem. Soc. 1959, 3144. Diels-Alder additions to tetrahydro-1,1′-binaphthyl: (h) Minuti, L.; Taticchi, A.; Marrocchi, A.; Gacs-Baitz, E. Tetrahedron 1997, 53, 6873. Altman, Y.; Ginsburg, D. J. Chem. Soc. 1959, 466, and references therein.
20. (a) Yang, B.; Liu, L.; Katz, T. J.; Liberko, C. A.; Miller, L. L. J. Am. Chem. Soc. 1991, 113, 8993.
21. (b) Liu, L.; Katz, T. J. Tetrahedron Lett. 1990, 31, 3983.
22. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
23. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
24. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
25. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
26. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
27. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
28. For the few functionalized examples known until recently, see footnote 4 of ref 7b. In addition, pyridine-containing helicenes: (a) Reference 6a. (b) Bell, T. W.; Jousselin, J. Am. Chem. Soc. 1991, 113, 6283. (c) Deshayes, K.; Broene, R. D.; Chao, I.; Knobler, C. B.; Diederich, F. J. Org. Chem. 1991, 56, 6787. Helicenecarboxylic acid derivatives: (d) Owens, L.; Thilgen, C.; Diedrich, F.; Knobler, C. B. Helv. Chim. Acta 1993, 76, 2757. (e) Frimer, A. A.; Kinder, J. D.; Youngs, W. J.; Meador, M. A. B. J. Org. Chem. 1995, 60, 1658. A phosphine: (f) Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 79. (g) Reetz, M. T.; Beuttenmüller, E. W.; Goddard, R. Tetrahedron Lett. 1997, 38, 3211. [5]-, [6]-, [7]-, and [8]helicenebisquinones: ref 7.
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73. 22 eliminates methanol from dimethyl acetals; (a) Miller, R. D.; McKean, D. R. Tetrahedron Lett. 1982, 23, 323. In other procedures, TMSI can be replaced as a reagent by TMSCl plus NaI: (b) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874. (c) Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1978, 2523. (d) Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai; H. Synthesis 1979, 379. (e) Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
74. 22 eliminates methanol from dimethyl acetals; (a) Miller, R. D.; McKean, D. R. Tetrahedron Lett. 1982, 23, 323. In other procedures, TMSI can be replaced as a reagent by TMSCl plus NaI: (b) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874. (c) Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1978, 2523. (d) Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai; H. Synthesis 1979, 379. (e) Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
75. 22 eliminates methanol from dimethyl acetals; (a) Miller, R. D.; McKean, D. R. Tetrahedron Lett. 1982, 23, 323. In other procedures, TMSI can be replaced as a reagent by TMSCl plus NaI: (b) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874. (c) Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1978, 2523. (d) Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai; H. Synthesis 1979, 379. (e) Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
76. 22 eliminates methanol from dimethyl acetals; (a) Miller, R. D.; McKean, D. R. Tetrahedron Lett. 1982, 23, 323. In other procedures, TMSI can be replaced as a reagent by TMSCl plus NaI: (b) Monta, T.; Okamoto, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1978, 874. (c) Morita, T.; Okamoto, Y.; Sakurai, H. Tetrahedron Lett. 1978, 2523. (d) Morita, T.; Yoshida, S.; Okamoto, Y.; Sakurai; H. Synthesis 1979, 379. (e) Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
77. 5a,b only 14 specify the amounts of reagents used and the amounts of products obtained, and in these, the average yield per photocyclization was ≤66 mg and the average amount of solvent 1.2 L.
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92. Related reactions are Diels-Alder additions of benzynes and methyleneisoquinolines or related structures: (a) Saá, C.; Guitian, E.; Castedo, L.; Saá J. M. Tetrahedron Lett. 1985, 26, 4559. (b) Castedo, L.; Guitián, E.; Saá, C.; Suau, R.; Saá. J. M. Tetrahedron Lett. 1983, 24, 2107. (c) Atanes, N.; Castedo, L; Guitián, E.; Saá, C.; Saá, J. M.; Suau, R. J. Org. Chem. 1991, 56, 2984. (d) Castedo, L; Guitian, E. In Studies in Natural Products Chemistry, Volume 3: Stereoselective Synthesis (Part B); Rahman, A-u., Ed.: Elsevier: New York. 1989; pp 417-454.
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