Filipin III: Configuration assignment and confirmation by synthetic correlation

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4219-4231

  Richardson, Timothy I ^b   Rychnovsky, Scott D ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

FILIPIN; MACROLIDE; POLYENE ANTIBIOTIC AGENT;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0030018806     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960218x     Document Type: Article

References (51)

1. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
2. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
3. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
4. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
5. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
6. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
7. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
8. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
9. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
10. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
11. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
12. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
13. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
14. Configurational assignment by X-ray: (a) Amphotericin B, Mechlinski, H.; Schaffher, C. P.; Ganis, P.; Avitable, G. Tetrahedron Lett. 1970, 3873. (b) Roxaticin, Maehr, H.; Yang, R.; Hong, L.-N.; Liu, C.-M.; Hatada, M. H.; Todaro, L. J. J. Org. Chem. 1989, 54, 3816. Configuration by degradation, NMR analysis, and partial synthesis: (c) Mycoticin, Schreiber, S. L.; Goulet, M. T. Tetrahedron Lett. 1987, 28,6001. (d) Schreiber, S. L.; Goulet, M. T.; Sammakia, T. Tetrahedron Lett. 1987, 28, 6005. (e) Schreiber, S. L.; Goulet, M. T. J. Am. Chem. Soc. 1987, 109, 8120. (f) Nystatin, Lancelin, J.-M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4521. (g) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (h) Nicolaou, K. C.; Ahn, K. H. Tetrahedron Lett. 1989, 30, 1217. Partial structure of lienomycin: (i) Pawlak, J.; Nakanishi, K.; Iwashita, T.; Borowski, E. J. Org. Chem. 1987, 52, 2896. (j) Roflamycoin, Rychnovsky, S. D.; Griesgraber, G.; Schlegel, R. J. Am. Chem. Soc. 1994, 116, 2623. (k) Pentamycin, Oishi, T. Pure Appl. Chem. 1989, 61, 427. (l) Nakata, T.; Hata, N.; Suenaga, T.; Oishi T. In Abstract of Papers, 30th Symposium on the Chemistry of Natural Products, Fukuoka, Oct 1988, p 540. Configuration by NMR analysis: (m) Pimaricin, Lancelin, J.-M.; Beau, J.-M. J. Am. Chem. Soc. 1990, 112, 4060. (n) Candidin, Pawlak, J.; Sowinski, P.; Borowski, E.; Gariboldi, P. J. Antibiot. 1993, 46, 1598.
15. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945.
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38. Filipin complex was obtained from Sigma (F-9765) as a crude mixture containing ∼50% filipin III or from Upjohn (lot no. 2923-DEV-39) containing about ∼8% filipin III. It can be purified by reversed-phase preparative HPLC.
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46. 1H NMR integration of the major C16 methyl doublet at 1.29 ppm versus the minor C16 methyl doublet at 1.26 ppm.
47. 1H NMR analysis.
48. We thank Victor G. Young for determining the crystal structure of 26. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
49. Enantiomeric purity by analysis using a chiral GC column. See Experimental Section for details.
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