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Volumn 69, Issue 12, 2004, Pages 4126-4134

A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; DRUG PRODUCTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 2942564141     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0497499     Document Type: Conference Paper
Times cited : (55)

References (67)
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    • For multistep processes targeting this segment, see: (a) References 5-7
    • For multistep processes targeting this segment, see: (a) References 5-7.
  • 24
    • 0001088334 scopus 로고
    • Snieckus, V., Ed.; JAI Press: London
    • (b) Braun, M. In Advances in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press: London, 1992; Vol. 1, p 177.
    • (1992) Advances in Carbanion Chemistry , vol.1 , pp. 177
    • Braun, M.1
  • 27
    • 0000763561 scopus 로고    scopus 로고
    • (b) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
    • (1999) Chem. Rev. , vol.99 , pp. 1121-1162
    • Reetz, M.T.1
  • 29
    • 0037060019 scopus 로고    scopus 로고
    • For leading references to more recent methods for the preparation of N-methyl α-amino acids, see: (b) Cho, J. H.; Kim, B. M. Tetrahedron Lett. 2002, 43, 1273-1276.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1273-1276
    • Cho, J.H.1    Kim, B.M.2
  • 36
    • 0000012007 scopus 로고
    • For acetate aldol reactions with N-Boc α-aminoaldehydes, see: (a) Swing, W. R.; Joullie, M. M. Heterocycles 1988, 27, 2843-2850.
    • (1988) Heterocycles , vol.27 , pp. 2843-2850
    • Swing, W.R.1    Joullie, M.M.2
  • 45
    • 84986360495 scopus 로고
    • For achiral appendages used to sterically protect ketone and carboxylic acid carbonyls, see the following. 1,1,1-Triphenylmethyl group: (a) Seebach, D. ; Ertas, M.; Locher, R.; Schweizer, W. B. Helv. Chim. Acta 1985, 68, 264-282.
    • (1985) Helv. Chim. Acta , vol.68 , pp. 264-282
    • Seebach, D.1    Ertas, M.2    Locher, R.3    Schweizer, W.B.4
  • 50
    • 2942594874 scopus 로고    scopus 로고
    • note
    • When N-deprotection was carried out on substrate I, pyrrolidine II was produced as major product. An X-ray crystal-structure analysis of II confirmed both structure and stereochemical assignment. We thank M. C. González-Rego for the synthesis of compounds I and II. [Diagram presented]
  • 51
  • 55
    • 85046528623 scopus 로고    scopus 로고
    • Catalytic hydrolysis of α-peptides by the action of CAN at reaction temperatures of about 50 °C has been reported recently: Takarada, T.; Yashiro, M.; Komiyama, M. Chem. Eur. J. 2000, 6, 3906-3913.
    • (2000) Chem. Eur. J. , vol.6 , pp. 3906-3913
    • Takarada, T.1    Yashiro, M.2    Komiyama, M.3
  • 61
    • 0010238774 scopus 로고
    • For reviews, see: (a) Back, T. G. Tetrahedron 1977, 33, 3041-3059.
    • (1977) Tetrahedron , vol.33 , pp. 3041-3059
    • Back, T.G.1
  • 63
    • 2942533078 scopus 로고    scopus 로고
    • Reference 8
    • (c) Reference 8.
  • 66
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    • note
    • The corresponding (E)-phenyl-2-pyridyl O-acyl oxime of acid 20 also furnished the desired cyclisized product in 40-45% yields.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.