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Volumn 10, Issue 1, 2008, Pages 137-140

Anti aldol selectivity in a synthetic approach to the C1-C 12 fragment of the tedanolides

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; KETONE; LACTONE; TEDANOLIDE; UNCLASSIFIED DRUG;

EID: 38349125118     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702729u     Document Type: Article
Times cited : (16)

References (30)
  • 3
    • 33750434287 scopus 로고    scopus 로고
    • Total synthesis of tedanolide: Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. J. Am. Chem. Soc. 2006, 128, 14038.
    • (a) Total synthesis of tedanolide: Ehrlich, G.; Hassfeld, J.; Eggert, U.; Kalesse, M. J. Am. Chem. Soc. 2006, 128, 14038.
  • 4
    • 20544461187 scopus 로고    scopus 로고
    • Synthetic study of tedanolide: Iwata, Y.; Tanino, K.; Miyashita, M. Org. Lett. 2005, 7, 2341.
    • (b) Synthetic study of tedanolide: Iwata, Y.; Tanino, K.; Miyashita, M. Org. Lett. 2005, 7, 2341.
  • 21
    • 0000796418 scopus 로고
    • Formation and Addition Reactions of Enol Ethers
    • Ch. 2.3
    • (b) Chan, T.-H. Formation and Addition Reactions of Enol Ethers. In Comp. Org. Synth. 1991, Ch. 2.3, 595.
    • (1991) Comp. Org. Synth , pp. 595
    • Chan, T.-H.1
  • 22
    • 0001316868 scopus 로고
    • Asymmetric Synthesis with Enol Ethers
    • Ch. 2.4
    • (c) Gennari, C. Asymmetric Synthesis with Enol Ethers. In Comp. Org. Synth. 1991, Ch. 2.4, 629.
    • (1991) Comp. Org. Synth , pp. 629
    • Gennari, C.1
  • 23
    • 38349173757 scopus 로고    scopus 로고
    • Ethylmagnesium bromide was added to the aldehyde 8 followed by Dess-Martin oxidation to the ketone. Reductive ring-opening with zinc in acetic acid and silylation of the diol with TBSCl gave 7.
    • Ethylmagnesium bromide was added to the aldehyde 8 followed by Dess-Martin oxidation to the ketone. Reductive ring-opening with zinc in acetic acid and silylation of the diol with TBSCl gave 7.
  • 27
    • 38349100639 scopus 로고    scopus 로고
    • Extensive decoupling experiments were carried out to ensure the identity of the indicated protons in all the acetonides
    • Extensive decoupling experiments were carried out to ensure the identity of the indicated protons in all the acetonides.
  • 30
    • 38349187776 scopus 로고    scopus 로고
    • These calculations were done on a simpler model system where the enol silyl ether was replaced by an enol, the OTBDPS group by an OH, and the OBn by an OMe group with the R group being ethyl R, Et
    • These calculations were done on a simpler model system where the enol silyl ether was replaced by an enol, the OTBDPS group by an OH, and the OBn by an OMe group with the R group being ethyl (R = Et).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.