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Volumn 6, Issue 8, 1998, Pages 1243-1254

Total synthesis and stereochemistry of cytoblastin

Author keywords

Cytoblastin; Natural products; Protein kinase C; Tumor promoters

Indexed keywords

CYTOBLASTIN; DIACYLGLYCEROL; INDOLACTAM V; INDOLE DERIVATIVE; PROTEIN KINASE C; UNCLASSIFIED DRUG;

EID: 0031704435     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)00113-8     Document Type: Article
Times cited : (6)

References (33)
  • 3
    • 0026513625 scopus 로고
    • For reviews on this work, see:
    • Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672. For reviews on this work, see: Rando, R. R.; Kishi, Y. Biochemistry 1992, 31, 2211; Kishi, Y.; Rando, R. R. Acc. Chem. Res. 1998, 31, 163.
    • (1992) Biochemistry , vol.31 , pp. 2211
    • Rando, R.R.1    Kishi, Y.2
  • 4
    • 0000306618 scopus 로고    scopus 로고
    • Nakamura, H.; Kishi, Y.; Pajares, M. A.; Rando, R. R. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672. For reviews on this work, see: Rando, R. R.; Kishi, Y. Biochemistry 1992, 31, 2211; Kishi, Y.; Rando, R. R. Acc. Chem. Res. 1998, 31, 163.
    • (1998) Acc. Chem. Res. , vol.31 , pp. 163
    • Kishi, Y.1    Rando, R.R.2
  • 7
    • 0345330021 scopus 로고    scopus 로고
    • These models are quoted in reviews cited under reference .
    • These models are quoted in reviews cited under reference .
  • 9
    • 0344467253 scopus 로고    scopus 로고
    • The numbering system adopted in this paper corresponds to that of cytoblastin.
    • The numbering system adopted in this paper corresponds to that of cytoblastin.
  • 10
    • 0029832318 scopus 로고    scopus 로고
    • (a) Preliminary results were communicated in
    • (a) Preliminary results were communicated in J. Am. Chem. Soc. 1996, 118, 8180.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 8180
  • 11
    • 0344467251 scopus 로고    scopus 로고
    • (b) This paper is largely based on the Dissertation of Harvard University, July
    • (b) This paper is largely based on the Dissertation of Moreno, O. A., Harvard University, July, 1996.
    • (1996)
    • Moreno, O.A.1
  • 16
    • 0344899019 scopus 로고    scopus 로고
    • When the addition failed, the epoxide was quantitatively rearranged to the homobenzylic ketone.
    • When the addition failed, the epoxide was quantitatively rearranged to the homobenzylic ketone.
  • 17
  • 19
    • 0344036115 scopus 로고    scopus 로고
    • 2.
    • 2.
  • 21
    • 0344467250 scopus 로고    scopus 로고
    • N-SEM-7-bromo-IL-V was chosen because we had previously encountered difficulty isolating the corresponding N-SEM-7-iodo-IL-V.
    • N-SEM-7-bromo-IL-V was chosen because we had previously encountered difficulty isolating the corresponding N-SEM-7-iodo-IL-V.
  • 22
    • 0025150557 scopus 로고
    • (-)-IL-V was prepared from L-tryptophan methyl ester, according to the reported method:
    • (-)-IL-V was prepared from L-tryptophan methyl ester, according to the reported method: Kogan, T. P.; Somers, T. C.; Venuti, M. C. Tetrahedron 1990, 46, 6623.
    • (1990) Tetrahedron , vol.46 , pp. 6623
    • Kogan, T.P.1    Somers, T.C.2    Venuti, M.C.3
  • 24
    • 0344899017 scopus 로고    scopus 로고
    • The electronic and steric effects of allylstannanes were tested; the coupling with α-acetoxy, α-methoxy, and α-t-butyldimethylsilyloxyallylstannanes resulted in exclusive formation of 15, whereas tri-sec-butylstannane resulted in a 5/1 mixture of 14 and 15.
    • The electronic and steric effects of allylstannanes were tested; the coupling with α-acetoxy, α-methoxy, and α-t-butyldimethylsilyloxyallylstannanes resulted in exclusive formation of 15, whereas tri-sec-butylstannane resulted in a 5/1 mixture of 14 and 15.
  • 27
    • 0001247835 scopus 로고
    • (b) For examples for the use of TMEDA or related diamines for low-temperature osmylation, see:
    • (b) For examples for the use of TMEDA or related diamines for low-temperature osmylation, see: Wang, Y.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 468.
    • (1992) J. Org. Chem. , vol.57 , pp. 468
    • Wang, Y.1    Babirad, S.A.2    Kishi, Y.3
  • 29
    • 0344899016 scopus 로고    scopus 로고
    • The extensive mechanistic studies conducted suggest that the observed regioselectivity of the coupling towards the desired adduct arises during the initial transmetallation step, whereas net leakage through a π-allylpalladium intermediate goes unilaterally towards the undesired adduct (ref b).
    • The extensive mechanistic studies conducted suggest that the observed regioselectivity of the coupling towards the desired adduct arises during the initial transmetallation step, whereas net leakage through a π-allylpalladium intermediate goes unilaterally towards the undesired adduct (ref b).
  • 31
    • 0344467247 scopus 로고    scopus 로고
    • We are indebted to Drs. Kumagai and Naganawa at Microbial Chemistry Research Foundation for a sample of natural cytoblastin.
    • We are indebted to Drs. Kumagai and Naganawa at Microbial Chemistry Research Foundation for a sample of natural cytoblastin.
  • 32
    • 0344036114 scopus 로고    scopus 로고
    • MacroModel version 45 provided courtesy of Professor Still, Columbia University Minimizations were performed on a Silicon Graphics Indigo workstation.
    • MacroModel version 45 provided courtesy of Professor Still, Columbia University Minimizations were performed on a Silicon Graphics Indigo workstation.
  • 33
    • 0344467246 scopus 로고    scopus 로고
    • Assays performed by Professor Rando at Harvard Medical School and by Dr Gusovsky at Eisai Research Institute.
    • Assays performed by Professor Rando at Harvard Medical School and by Dr Gusovsky at Eisai Research Institute.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.