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Volumn 129, Issue 5, 2007, Pages 1050-1051

Total syntheses of durgamone, nakorone, and abudinol B via biomimetic oxa- and carbacyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ABUDINOL B; DURGAMONE; NAKORONE; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33846799213     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja068826+     Document Type: Article
Times cited : (58)

References (33)
  • 8
    • 33745700292 scopus 로고    scopus 로고
    • Due to the availability of 1,2:4,5-di-O-isopropylidene-D-erythro-2,3-hexodiuro-2,6-pyranose Shi catalyst from D-fructose, we elected to prepare the enantiomers of natural products 2-4. However, an improved preparation for L-fructose is now available for the enantiomeric catalyst. See: Zhao, M.-X.; Shi, Y. J. Org. Chem. 2006, 71, 5377.
    • (c) Due to the availability of 1,2:4,5-di-O-isopropylidene-D-erythro-2,3-hexodiuro-2,6-pyranose "Shi catalyst" from D-fructose, we elected to prepare the enantiomers of natural products 2-4. However, an improved preparation for L-fructose is now available for the enantiomeric catalyst. See: Zhao, M.-X.; Shi, Y. J. Org. Chem. 2006, 71, 5377.
  • 9
    • 33846843469 scopus 로고
    • For enolsilanes as terminating nucleophiles in polyene cyclizations, see: a
    • For enolsilanes as terminating nucleophiles in polyene cyclizations, see: (a) Corey, E. J.; Sodeoka, M. Tetrahedron Lett. 1991, 32, 1005.
    • (1991) Tetrahedron Lett , vol.32 , pp. 1005
    • Corey, E.J.1    Sodeoka, M.2
  • 13
    • 33846843470 scopus 로고    scopus 로고
    • 2AICl or TBSOTf favored formation of the silyl ether 10.
    • 2AICl or TBSOTf favored formation of the silyl ether 10.
  • 14
    • 33846789133 scopus 로고    scopus 로고
    • See Supporting Information for details on the crystallographic analyses
    • See Supporting Information for details on the crystallographic analyses.
  • 15
    • 33846823517 scopus 로고    scopus 로고
    • We observed substantial differences in optical rotations for synthetic ent-2, ent-3, and ent-4 when compared with reported values for the corresponding natural products 2, 3, and 4. However, spectroscopic data for our synthetic compounds are in good agreement with the natural products (see Supporting Information).
    • We observed substantial differences in optical rotations for synthetic ent-2, ent-3, and ent-4 when compared with reported values for the corresponding natural products 2, 3, and 4. However, spectroscopic data for our synthetic compounds are in good agreement with the natural products (see Supporting Information).
  • 18
    • 0000732375 scopus 로고    scopus 로고
    • For examples of mechanistically similar ring contractions, see: (c) Hayashi, N, Fujiwara, K, Murai, A. Synlett 1997, 793
    • For examples of mechanistically similar ring contractions, see: (c) Hayashi, N.; Fujiwara, K.; Murai, A. Synlett 1997, 793.
  • 21
    • 33846844062 scopus 로고    scopus 로고
    • 3P (1.2 equiv), NBS (1.1 equiv), THF, 0°C.
    • 3P (1.2 equiv), NBS (1.1 equiv), THF, 0°C.
  • 32
    • 33846792452 scopus 로고    scopus 로고
    • Diene 24 was also obtained from initial conversion of enol triflate 23 to the vinylboronate, followed by cross-coupling with enol triflate 22, but the yields of 24 were substantially lower (38-42%) from this route.
    • Diene 24 was also obtained from initial conversion of enol triflate 23 to the vinylboronate, followed by cross-coupling with enol triflate 22, but the yields of 24 were substantially lower (38-42%) from this route.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.