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Volumn 72, Issue 11, 2007, Pages 4205-4212

Hetero Diels-Alder synthesis of 3-hydroxypyridines: Access to the nosiheptide core

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; ISOMERS; OPTIMIZATION; SYNTHESIS (CHEMICAL);

EID: 34249819690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0703505     Document Type: Article
Times cited : (68)

References (54)
  • 8
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    • Some examples: (a) Harris, S. A.; Folkers, K. J. Am. Chem. Soc. 1939, 61, 1245.
    • Some examples: (a) Harris, S. A.; Folkers, K. J. Am. Chem. Soc. 1939, 61, 1245.
  • 11
    • 34249815384 scopus 로고    scopus 로고
    • This work was presented in part at the Glaxo/Dortmund symposium on Chemical Biology. Stevenage, UK 2005
    • This work was presented in part at the Glaxo/Dortmund symposium on Chemical Biology. Stevenage, UK 2005.
  • 14
    • 33748057815 scopus 로고    scopus 로고
    • Concurrent with this work, some related efforts have been reported: Fletcher, M. D.; Hurst, T. E.; Miles, T. J.; Moody, C. J. Tetrahedron 2006, 62, 5454.
    • (c) Concurrent with this work, some related efforts have been reported: Fletcher, M. D.; Hurst, T. E.; Miles, T. J.; Moody, C. J. Tetrahedron 2006, 62, 5454.
  • 15
    • 34249774755 scopus 로고    scopus 로고
    • Selected overviews: (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Permagon Press: Oxford, 1991; 5, pp 315-401.
    • Selected overviews: (a) Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Permagon Press: Oxford, 1991; Vol 5, pp 315-401.
  • 27
    • 33745685959 scopus 로고    scopus 로고
    • For an organocatalytic variant see
    • (c) For an organocatalytic variant see He, M.; Struble, J. R.; Bode, J. W. J. Am. Chem. Soc. 2006, 128, 8418.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8418
    • He, M.1    Struble, J.R.2    Bode, J.W.3
  • 28
    • 34249817452 scopus 로고    scopus 로고
    • Tautomer formation. Data not shown
    • Tautomer formation. Data not shown.
  • 31
    • 34249807784 scopus 로고    scopus 로고
    • See supporting information for details
    • See supporting information for details.
  • 33
  • 34
    • 34249813594 scopus 로고    scopus 로고
    • In our hands, both 3-O-TMS- and TES-protected 3-hydroxypyridines were unstable to standard aqueous workup conditions as well as standard SiO 2-based purification TLC and flash column chromatography
    • 2-based purification (TLC and flash column chromatography).
  • 35
    • 34249814488 scopus 로고    scopus 로고
    • All regioisomers have been unequivocally assigned by means of 2-D NMR data (DQF-COSY, HSQC, HMBC).
    • All regioisomers have been unequivocally assigned by means of 2-D NMR data (DQF-COSY, HSQC, HMBC).
  • 39
    • 0000763939 scopus 로고    scopus 로고
    • We have not succeeded in securing proof for the intermediacy of alkyne 15, but β-eliminations of enol ethers have considerable precedence; see for example (a) Hargrove, R. J, Stang, P. J. J. Org. Chem. 1974, 39, 581
    • We have not succeeded in securing proof for the intermediacy of alkyne 15, but β-eliminations of enol ethers have considerable precedence; see for example (a) Hargrove, R. J.; Stang, P. J. J. Org. Chem. 1974, 39, 581.
  • 50
    • 0029952823 scopus 로고    scopus 로고
    • When compared with other α-amino acids, pseudo-prolines (ketal-protected serine, threonine and cysteine derivatives) have, such as proline itself, a much lower tendency to racemize at the α-carbon; for example see Wöhr, T.; Wahl, T.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X. C.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218.
    • When compared with other α-amino acids, pseudo-prolines (ketal-protected serine, threonine and cysteine derivatives) have, such as proline itself, a much lower tendency to racemize at the α-carbon; for example see Wöhr, T.; Wahl, T.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X. C.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218.
  • 53
    • 0031878288 scopus 로고    scopus 로고
    • A different approach to the nosiheptide core structure has been detailed, (a) Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G. Bull. Chem. Soc. Jpn. 1998, 71, 1391.
    • A different approach to the nosiheptide core structure has been detailed, (a) Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G. Bull. Chem. Soc. Jpn. 1998, 71, 1391.
  • 54
    • 34249784697 scopus 로고    scopus 로고
    • See also ref 8b
    • (b) See also ref 8b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.