Determination of absolute structure of macroviracins by chemical synthesis

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1555-1558

  Takahashi, Shunya ^a   Hosoya, Moritoshi ^a   Koshino, Hiroyuki ^a   Nakata, Tadashi ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CARBOXYLIC ACID; ESTER DERIVATIVE; FATTY ACID; MACROCYCLIC COMPOUND; MACROVIRACIN A; MACROVIRACIN B 1; MACROVIRACIN B 2; MACROVIRACIN B 3; MACROVIRACIN C 1; MACROVIRACIN C 2; MACROVIRACIN C 3; MACROVIRACIN D; METHYL GROUP; UNCLASSIFIED DRUG; OLIGOSACCHARIDE;

ARTICLE; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROBORATION; IODINATION; STEREOCHEMISTRY; CHEMISTRY; MACROMOLECULE; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

FATTY ACIDS; MACROMOLECULAR SUBSTANCES; OLIGOSACCHARIDES; STEREOISOMERISM; STREPTOMYCES;

EID: 0042265615     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034338k     Document Type: Article

References (19)

1. Hyodo, T.; Tsuchiya, Y.; Sekine, A.; Amano, T. Jpn. Kokai Tokkyo Koho Jpn. Pat. 11246587, Sept 14, 1999.
2. Tsunakawa, M.; Komiyama, N.; Tenmyo, O.; Tomita, K.; Kawano, K.; Kotake, C.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1467-1471. Tsunakawa, M.; Kotake, C.; Yamasaki, T.; Moriyama, T.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1472-1480.
3. Tsunakawa, M.; Komiyama, N.; Tenmyo, O.; Tomita, K.; Kawano, K.; Kotake, C.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1467-1471. Tsunakawa, M.; Kotake, C.; Yamasaki, T.; Moriyama, T.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1472-1480.
4. Uyeda, M.; Yokomizo, K.; Miyamoto, Y.; Habib, E.-S. E. J. Antibiot. 1998, 51, 823-828. Yokomizo, K.; Miyamoto, Y.; Nagao, K.; Kumagae, E.; Habib, E.-S. E.; Suzuki, K.; Harada, S.; Uyede, M. J. Antibiot. 1998, 51, 1035-1039. Habib, E.-S. E.; Yokomizo, K.; Murata, K.; Uyeda, M. J. Antibiot. 2000, 53 1420-1423.
5. Uyeda, M.; Yokomizo, K.; Miyamoto, Y.; Habib, E.-S. E. J. Antibiot. 1998, 51, 823-828. Yokomizo, K.; Miyamoto, Y.; Nagao, K.; Kumagae, E.; Habib, E.-S. E.; Suzuki, K.; Harada, S.; Uyede, M. J. Antibiot. 1998, 51, 1035-1039. Habib, E.-S. E.; Yokomizo, K.; Murata, K.; Uyeda, M. J. Antibiot. 2000, 53 1420-1423.
6. Uyeda, M.; Yokomizo, K.; Miyamoto, Y.; Habib, E.-S. E. J. Antibiot. 1998, 51, 823-828. Yokomizo, K.; Miyamoto, Y.; Nagao, K.; Kumagae, E.; Habib, E.-S. E.; Suzuki, K.; Harada, S.; Uyede, M. J. Antibiot. 1998, 51, 1035-1039. Habib, E.-S. E.; Yokomizo, K.; Murata, K.; Uyeda, M. J. Antibiot. 2000, 53 1420-1423.
7. Fürstner, A.; Albert, M.; Mlynarski, J.; Matheu, M. J. Am. Chem. Soc. 2002, 124, 1168-1169. Fürstner, A.; Mlynarski, J.; Albert, M. J. Am. Chem. Soc. 2002, 124, 10274-10275.
8. Fürstner, A.; Albert, M.; Mlynarski, J.; Matheu, M. J. Am. Chem. Soc. 2002, 124, 1168-1169. Fürstner, A.; Mlynarski, J.; Albert, M. J. Am. Chem. Soc. 2002, 124, 10274-10275.
9. For a method for determination of the absolute configuration of secondary alcohols by using benzoylated sugars, see: Trujillo, M.; Morales, E. Q.; Vázquez, J. T. J. Org. Chem. 1994, 59, 6637-6642.
10. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719-2722.
11. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
12. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
13. 3, respectively, at 23 ± 2°.
14. 10 of this compound failed.
15. Mitsunobu, O. Synthesis 1981, 1-28.
16. Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145-6148.
17. Fukui, H.; Tsuchiya, Y.; Fujita, K.; Nakagawa, T.; Koshino, H.; Nakatta, T. Bioorg. Med. Chem. Lett. 1997, 7, 2081-2086.
18. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404-5406.
19. From the results of several model experiments, we expected that benzoylation at the C-2 position would proceed regioselectively.