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Volumn 121, Issue 10, 1999, Pages 2147-2155

Total synthesis of spirotryprostatin A, leading to the discovery of some biologically promising analogues

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; SPIROTRYPROSTATIN A; UNCLASSIFIED DRUG;

EID: 0033577262     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja983788i     Document Type: Article
Times cited : (456)

References (34)
  • 10
    • 0001048369 scopus 로고
    • The Pictet-Spengler reaction of 8 and 38 with 10 has been reported: (a) Harrison, D. M.; Sharma, R. B. Tetrahedron Lett. 1986, 27, 521. (b) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron 1988, 44, 359.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 521
    • Harrison, D.M.1    Sharma, R.B.2
  • 11
    • 0023850429 scopus 로고
    • The Pictet-Spengler reaction of 8 and 38 with 10 has been reported: (a) Harrison, D. M.; Sharma, R. B. Tetrahedron Lett. 1986, 27, 521. (b) Kodato, S.; Nakagawa, M.; Hongu, M.; Kawate, T.; Hino, T. Tetrahedron 1988, 44, 359.
    • (1988) Tetrahedron , vol.44 , pp. 359
    • Kodato, S.1    Nakagawa, M.2    Hongu, M.3    Kawate, T.4    Hino, T.5
  • 13
    • 4243241249 scopus 로고
    • For lead references of the Pictet-Spengler reaction to synthesize cis and trans tetrahydrocarbolines, see: (a) Cox, E. D.; Hamaker, L. K.; Li, J.; Yu, P.; Czerwinski, K. M.; Deng., L.; Bennett, D. W.; Cook, J. M.; Watson, W. H.; Krawlec, M. J. Org. Chem. 1997, 62, 44. (b) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
    • (1995) Chem. Rev. , vol.95 , pp. 1797
    • Cox, E.D.1    Cook, J.M.2
  • 23
    • 13044299349 scopus 로고    scopus 로고
    • note
    • 2; then TBSCl, imid, DMF. Attempts to oxidatively rearrange this molecule resulted in complicated mixtures and loss of silicon.
  • 24
    • 13044315413 scopus 로고    scopus 로고
    • note
    • An observation of molecular models reveals that the corresponding trans ring fusion, resulting from attack of water on the α-face of 21, would be a highly strained molecule and, thus, less likely to form.
  • 27
    • 13044314603 scopus 로고    scopus 로고
    • note
    • In part, the difficulty in oxidizing of 30 is due to the poor solubility of this molecule in organic solvents. Advantage was taken in the model system (Scheme 7) of the more desirable solubility properties that these molecules possess prior to diketopiperazine formation.
  • 28
    • 13044298733 scopus 로고    scopus 로고
    • note
    • Spectral data of naturally occurring 1 were kindly provided by Professor Osada.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.