A Flexible Approach to (S)-5-Alkyl Tetramic Acid Derivatives: Application to the Asymmetric Synthesis of (+)-Preussin and Protected (3S,4S)-AHPPA

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4341-4344

  Huang, Pei Qiang ^a   Wu, Tian Jun ^a   Ruan, Yuan Ping ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 3 HYDROXY 5 PHENYLVALERIC ACID; ANTIFUNGAL AGENT; PREUSSIN; TETRAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0344927927     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035617a     Document Type: Article

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34. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
35. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
36. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
37. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
38. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
39. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
40. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
41. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
42. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
43. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
44. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
45. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
46. For the asymmetric syntheses of preussin, see: (a) Pak, C. W.; Lee, G. H. J. Org. Chem. 1991, 56, 1128. (b) McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485. (c) Deng, W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721. (e) Yoda, H.; Yamazaki, H.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 373. (f) Verma, R. ; Ghosh, S. K. Chem. Commun. 1997, 1601. (g) Beier, C., Schaumann, E. Synthesis 1997, 1296. (h) Kadota, I.; Saya, S.; Yamamoto, Y. Heterocycles 1997, 46, 335. (i) Armas, P. D.; Tellado-Garcia, F.; Tellado-Marrero, J. J.; Robles, J. Tetrahedron Lett. 1998, 39, 131. (j) Dong, H. Q.; Lin, G. Q. Chin. J. Chem. 1998, 16, 458. (k) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63. 4660. (l) Veeresa; G.; Datta, A. Tetrahedron 1998, 54, 15673. (m) Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041. (n) Okue, M.; Watanabe, H.; Kitahara, T. Tetrahedron 2001, 57, 4107.
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49. For other non-amino-acid-based synthetic approaches to AHPPA and derivatives, see: (a) Yanagisawa, H.; Kanazaki, T.; Nishi, T. Chem. Lett. 1989, 687. (b) Enders. D.; Reinhold: U. Angew. Chem. 1995, 107, 1322; Enders, D.; Reinhold: U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (c) Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428. (d) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419 and references therein.
50. For other non-amino-acid-based synthetic approaches to AHPPA and derivatives, see: (a) Yanagisawa, H.; Kanazaki, T.; Nishi, T. Chem. Lett. 1989, 687. (b) Enders. D.; Reinhold: U. Angew. Chem. 1995, 107, 1322; Enders, D.; Reinhold: U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (c) Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428. (d) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419 and references therein.
51. For other non-amino-acid-based synthetic approaches to AHPPA and derivatives, see: (a) Yanagisawa, H.; Kanazaki, T.; Nishi, T. Chem. Lett. 1989, 687. (b) Enders. D.; Reinhold: U. Angew. Chem. 1995, 107, 1322; Enders, D.; Reinhold: U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (c) Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428. (d) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419 and references therein.
52. For other non-amino-acid-based synthetic approaches to AHPPA and derivatives, see: (a) Yanagisawa, H.; Kanazaki, T.; Nishi, T. Chem. Lett. 1989, 687. (b) Enders. D.; Reinhold: U. Angew. Chem. 1995, 107, 1322; Enders, D.; Reinhold: U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (c) Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428. (d) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419 and references therein.
53. For other non-amino-acid-based synthetic approaches to AHPPA and derivatives, see: (a) Yanagisawa, H.; Kanazaki, T.; Nishi, T. Chem. Lett. 1989, 687. (b) Enders. D.; Reinhold: U. Angew. Chem. 1995, 107, 1322; Enders, D.; Reinhold: U. Angew. Chem., Int. Ed. Engl. 1995, 34, 1219. (c) Doi, T.; Kokubo, M.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1998, 63, 428. (d) Aoyagi, Y.; Williams, R. M. Tetrahedron 1998, 54, 10419 and references therein.
54. Omura, S.; Imamura, N.; Kawakita, K.; Mori, Y.; Yamazaki, Y.; Masuma, R. ; Takahashi, Y.; Tanaka, H.; Huang, L.-Y.; Woodruff, H. J. Antibiot. 1986, 39, 1079.