Glycocinnasperimicin D Synthetic Studies: Synthesis of Cinnamoyl Glycosides via Iodination-Heck Reaction Sequence Starting from Phenyl Glycosides

Synlett

Volumn , Issue 1, 2004, Pages 89-92

  Nishiyama, Taihei ^a   Ichikawa, Yoshiyasu ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Antibiotics; Cinnamoyl glycoside; Glycosylation; Heck reaction; Palladium

Indexed keywords

ANTIBIOTIC AGENT; GLYCOCINNASPERIMICIN D; GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; IODINATION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0348231802     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43376     Document Type: Article

References (19)

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3. (3) For the synthetic studies of LL-BM123β, see the references: (a) Araki, K.; Miyazawa, K.; Hashimoto, H.; Yoshimura, J. Tetrahedron Lett. 1982, 23, 1705. (b) Araki, K.; Kawa, M.; Saito, Y.; Hashimoto, H.; Yoshimura, J. Bull. Chem. Soc, Jpn. 1986, 59, 3137. (c) Araki, K.; Hashimoto, H.; Yoshimura, J. Carbohydr. Res. 1982, 109, 143.
4. For the synthetic studies of LL-BM123β, see the references: (a) Araki, K.; Miyazawa, K.; Hashimoto, H.; Yoshimura, J. Tetrahedron Lett. 1982, 23, 1705. (b) Araki, K.; Kawa, M.; Saito, Y.; Hashimoto, H.; Yoshimura, J. Bull. Chem. Soc, Jpn. 1986, 59, 3137. (c) Araki, K.; Hashimoto, H.; Yoshimura, J. Carbohydr. Res. 1982, 109, 143.
5. For the synthetic studies of LL-BM123β, see the references: (a) Araki, K.; Miyazawa, K.; Hashimoto, H.; Yoshimura, J. Tetrahedron Lett. 1982, 23, 1705. (b) Araki, K.; Kawa, M.; Saito, Y.; Hashimoto, H.; Yoshimura, J. Bull. Chem. Soc, Jpn. 1986, 59, 3137. (c) Araki, K.; Hashimoto, H.; Yoshimura, J. Carbohydr. Res. 1982, 109, 143.
6. (a) Oyama, K.; Kondo, T. Synlett 1999, 1627; and references therein,
7. (b) See also ref.3c
8. We avoid glycosylation with iodophenol, because our preliminary experiments showed that catalytic hydrogenolysis of 6-iodo-glycopyranose is the most simple and high-yielding method for multigram synthesis of 6-deoxy glycopyranose. For recent examples of C6-deoxygenation: Medgyes, A.; Farkas, E. ; Liptak, A.; Pozsgay, V. Tetrahedron 1997, 53, 4159.
9. This acid-catalyzed glycosylation initially led to the formation of an anomeric mixture of phenyl galactosides. Prolonged reaction time (4 d) resulted in a gradual decrease of the β-isomer proportion and concomitant increase in the formation of α-anomer.
10. Sugiyama, T. Bull. Chem. Soc. Jpn. 1981, 54, 2847.
11. 2, -5 °C) and the Heck reaction of the resultant brominated glycosylated aromatic with alkenes has been reported by Lepoittevin et al.: Mabic, S.; Lepoittevin, J.-P. Tetrahedron Lett. 1995, 36, 1705.
12. (b) In our case, bromophenyl glycosides, prepared (NBS, DMF, r.t.) in good yields, were found to be poor substrates for the Heck reaction.
13. Although cinnamoyl glycosides are known as important natural products, their synthesis suffer from the low nucleophilicity of p-hydroxycinnamic acid derivatives. For example: Takada, N.; Kato, E.; Ueda, K.; Yamamura, S.; Ueda, M. Tetrahedron Lett. 2002, 43, 7655.
14. 2O (Scheme 5). (Equation Presented)
15. 3, 75 MHz): δ = 17.1, 20.47, 20.53, 25.5, 27.2, 27.5, 28.19, 28.23, 35.6, 39.9, 43.2, 46.5, 52.3, 53.9, 66.3, 70.7, 73.1, 79.0, 79.7, 95.6, 116.4, 120.2, 129.2, 129.8, 139.4, 156.0, 156.5, 157.0, 166.1, 169.7, 171.2.
16. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 23, 4467.
17. (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Tohda, Y.; Hagihara, N. Synthesis 1980, 627.
18. For recent examples of the Sonogashira reacton using iodophenyl α-D-mannopyranoside for the efficient synthesis of sugar-rods and cyclodextrin-based cluster mannosides, see: (a) Roy, R.; Das, S. K.; Santoyo-Gonzalez, F.; Hernandez-Mateo, F.; Dam, T. K.; Brewer, C. F. Chem. -Eur. J. 2000, 6, 1757. (b) Ortega-Caballero, F.; Gimenez-Martinez, J. J.; Vargas-Berenguel, A. Org. Lett. 2003, 14, 2389.
19. For recent examples of the Sonogashira reacton using iodophenyl α-D-mannopyranoside for the efficient synthesis of sugar-rods and cyclodextrin-based cluster mannosides, see: (a) Roy, R.; Das, S. K.; Santoyo-Gonzalez, F.; Hernandez-Mateo, F.; Dam, T. K.; Brewer, C. F. Chem. - Eur. J. 2000, 6, 1757. (b) Ortega-Caballero, F.; Gimenez-Martinez, J. J.; Vargas-Berenguel, A. Org. Lett. 2003, 14, 2389.