Practical asymmetric approach to pyrrolidinones: Efficient synthesis of (+)-preussin and (-)-AHPPA

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4660-4663

  Kanazawa, Alice ^a   Gillet, Sandra ^a   Delair, Philippe ^a   Greene, Andrew E ^a  

^a UNIV GRENOBLE ALPES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; PYRROLIDINE DERIVATIVE;

ANTIFUNGAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; MYCOSIS; STEREOCHEMISTRY;

EID: 0032504134     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801162     Document Type: Article

References (57)

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2. For reviews on the occurrence, biological properties, and syntheses of pyrrolidines, see: Attygalle, A. B.; Morgan, D. E. Chem. Soc. Rev. 1984, 13, 245-278. Massiot, G.; Delaude, C. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 27, Chapter 3.
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7. Pyrrolizidines, see: Robins, D. J. Nat. Prod. Rep. 1992, 9, 313-321. Liddell, J. R. Ibid. 1997, 14, 653-660. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41. Michael, J. P. Ibid. 1997, 14, 619-636.
8. Pyrrolizidines, see: Robins, D. J. Nat. Prod. Rep. 1992, 9, 313-321. Liddell, J. R. Ibid. 1997, 14, 653-660. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41. Michael, J. P. Ibid. 1997, 14, 619-636.
9. Pyrrolizidines, see: Robins, D. J. Nat. Prod. Rep. 1992, 9, 313-321. Liddell, J. R. Ibid. 1997, 14, 653-660. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41. Michael, J. P. Ibid. 1997, 14, 619-636.
10. Pyrrolizidines, see: Robins, D. J. Nat. Prod. Rep. 1992, 9, 313-321. Liddell, J. R. Ibid. 1997, 14, 653-660. Indolizidines, see: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045-4066. Takahata, H.; Momose, T. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1993; Vol. 44, Chapter 3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 21-41. Michael, J. P. Ibid. 1997, 14, 619-636.
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17. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Wei, Z-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. Gennari, C.; Pain, G.; Moresca J. Org. Chem. 1995, 60, 6248-6249. Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148. (e) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211 and references therein.
18. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Wei, Z-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. Gennari, C.; Pain, G.; Moresca J. Org. Chem. 1995, 60, 6248-6249. Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148. (e) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211 and references therein.
19. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Wei, Z-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. Gennari, C.; Pain, G.; Moresca J. Org. Chem. 1995, 60, 6248-6249. Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148. (e) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211 and references therein.
20. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Wei, Z-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. Gennari, C.; Pain, G.; Moresca J. Org. Chem. 1995, 60, 6248-6249. Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148. (e) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211 and references therein.
21. For recent syntheses of chiral pyrrolidinones, see: (a) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36-42. (b) Wei, Z-Y.; Knaus, E. E. Tetrahedron Lett. 1993, 34, 4439-4442. Gennari, C.; Pain, G.; Moresca J. Org. Chem. 1995, 60, 6248-6249. Wee, A. G. H.; Liu, B. Tetrahedron Lett. 1996, 37, 145-148. (e) Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210-5211 and references therein.
22. (a) Schwartz, R. E.; Liesch, J.; Hensens, O.; Zitano, L.; Honeycutt, S.; Garrity, G.; Fromtling, R. A.; Onishi, J.; Monaghan, R. J. Antibiot. 1988, 41, 1774-1779.
23. Schwartz, R. E.; Onishi, J. C.; Monaghan, R. L.; Liesch, J. M.; Hensens, O. D. U.S. Patent 4,847,284, 1989.
24. (b) Johnson, J. H.; Philippson, D. W.; Kahle, A. D. J. Antibiot. 1989, 42, 1184-1185.
25. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
26. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
27. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
28. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
29. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
30. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
31. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
32. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
33. For previous syntheses of (+)-preussin from chiral pool starting material, see: (c) Pak, C. S.; Lee, G. H. J. Org. Chem. 1991, 56, 1128-1133. Shimazaki, M.; Okazaki, F.; Nakajima, F.; Ishikawa, T.; Ohta, A. Heterocycles 1993, 36, 1823-1836. (e) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489. (f) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241-11250. (g) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721-4722. (h) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373-374. Beier, C.; Schaumann, E. Synthesis 1997, 1296-1300. (j) de Armas, P.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131-134. For a synthesis based on desymmetrization of a meso anhydride, see: (k) Ghosh, S. K.; Verma, R. J. Chem. Soc., Chem. Commun. 1997, 1601-1602.
34. (a) Omura, S.; Imamura, N.; Kawakita, K.; Mori, Y.; Yamazaki, Y.; Masuma, R.; Takahashi, Y.; Tanaka, H.; Huang, L-Y.; Woodruff, H. B. J. Antibiot. 1986, 39, 1079-1085.
35. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
36. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
37. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
38. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
39. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
40. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
41. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
42. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
43. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
44. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
45. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
46. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
47. For previous syntheses and uses of AHPPA, see: (b) Rich, D. H.; Sun, E. T. O.; Ulm, E. J. Med. Chem. 1980, 23, 27-33. Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182. Raddatz, P.; Radunz, H.-E.; Schneider, G.; Schneider, G.; Schwartz, H. Angew. Chem., Int. Ed. Engl 1988, 27, 426-427. (e) Reetz, M. T.; Drewes, M. W.; Matthews, B. R.; Lennick, K. J. Chem. Soc., Chem. Commun. 1989, 1474-1475. (f) Moore, M. L.; Bryan, W. M.; Fakhoury, S. A.; Magaard, V. W.; Huffman, W. F.; Dayton, B. D.; Meek, T. D.; Hyland, L.; Dreyer, G. B.; Metcalf, B. W.; Strickler, J. E.; Gorniak, J. G.; Debouck, C. Biochem. Biophys. Res. Commun. 1989, 159, 420-425. (g) Nishi, T.; Saito, F.; Nagahori, H.; Kataoka, M.; Morisawa, Y.; Yabe, Y.; Sakurai, M.; Higashida, S.; Shoji, M.; Matsushita, Y.; Iijima, Y.; Ohizumi, K.; Koike, H. Chem. Pharm. Bull. 1990, 38, 103-109. (h) Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359-7362. McConnell, R. M.; Frizzell, D.; Camp, A.; Evans, A.; Jones, W.; Cagle, C. J. Med. Chem. 1991, 34, 2298-2300. (j) Shinozaki, K.; Mizuno, K.; Oda, H.; Masaki, Y. Chem. Lett. 1992, 2265-2268. (k) Kiyooka, S-i.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett. 1993, 36, 5729-5732. Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010-4012. Fugi, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Heterocycles 1996, 42, 701-722. (n) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201 and references therein.
48. Delair, P.; Kanazawa, A.; B. M. de Azevedo, M; Greene, A. E. Tetrahedron: Asymmetry 1996, 7, 2707-2710.
49. Kann, N.; Bernardes, V.; Greene, A. E. Org. Synth. 1997, 74, 13-22.
50. Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1-17.
51. Johnston, B. D.; Slessor, K. N.; Oehlschlager, A. C. J. Org. Chem. 1985, 50, 114-117.
52. Tilley, J. W.; Clader, J. W.; Wirkus, M.; Blount, J. F. J. Org. Chem. 1985, 50, 2220-2224.
53. Fristschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 1005-1006.
54. The corresponding imidoyl chloride could not be prepared. See: Engel, N.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 676.
55. Zegga, C. A.; Smith, M. B.; Ross, B. A.; Arhin, A.; Cronin, P. L. E. J. Org. Chem. 1984, 49, 4397-4399.
56. Hua, D. H.; Miao, S. W.; Bharathi, S. N.; Katshuhira, T.; Bravo, A. A. Ibid. 1990, 55, 3682-3684.
57. Borch, R. F.; Hassid, A. I. J. Org. Chem. 1972, 37, 1673-1674.