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Volumn 128, Issue 21, 2006, Pages 6931-6937

Synthesis of (-)-sordarin

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONFORMATIONS; HYDROXYAPATITE; NITROGEN COMPOUNDS; OLEFINS; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33744820012     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060408h     Document Type: Article
Times cited : (96)

References (54)
  • 5
    • 33744806798 scopus 로고
    • Ph.D. Dissertation, Eidgenossischen Technischen Hochschule, Zurich
    • Vasella, A. T. Ph.D. Dissertation, Eidgenossischen Technischen Hochschule, Zurich, 1972.
    • (1972)
    • Vasella, A.T.1
  • 7
    • 33744808733 scopus 로고    scopus 로고
    • note
    • The numbers on each carbon atom of intermediates 8, 13, 14, 18, 19, 20, 21, 33, and 34 correspond to those of sordaricin (2).
  • 11
    • 33744800178 scopus 로고
    • Ph.D. Dissertation, ETH, Zurich, Switzerland
    • Borschberg, H. J. Ph.D. Dissertation, ETH, Zurich, Switzerland, 1975.
    • (1975)
    • Borschberg, H.J.1
  • 16
    • 0346602829 scopus 로고
    • (b) Tsuji, J. Tetrahedron 1986, 42, 4361-4401.
    • (1986) Tetrahedron , vol.42 , pp. 4361-4401
    • Tsuji, J.1
  • 26
    • 33744826443 scopus 로고    scopus 로고
    • note
    • 2O, cat. DMAp→pyridine, rt, 2 h 95%
  • 27
    • 33744818366 scopus 로고    scopus 로고
    • CCDC-295066 contains the supplementary crystallographic data for compound 5. These data can be obtained free of charge via www. ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB21 EZ, U.K.; fax (+44)1223-336-033; or deposit@cdc.cam.ac.uk) .
  • 28
    • 33744800702 scopus 로고    scopus 로고
    • note
    • Synthetic schemes of the substrate 24 were depicted in the Supporting Information.
  • 29
    • 0037083881 scopus 로고    scopus 로고
    • There are some reports on the transition-metal catalyzed construction of bicyclo[2.2.1]heptan-2-one derivatives, see: (a) Langer, P.; Holtz, E.; Saleh, N. N. R. Chem.-Eur. J. 2002, 8, 917-928.
    • (2002) Chem.-Eur. J. , vol.8 , pp. 917-928
    • Langer, P.1    Holtz, E.2    Saleh, N.N.R.3
  • 32
    • 33744802117 scopus 로고    scopus 로고
    • note
    • This approach was carried out on racemic 5.
  • 37
    • 33744790792 scopus 로고    scopus 로고
    • note
    • In the absence of HMPA, the desired 29 was obtained only in 58% yield along with 35% yield of the hydride adduct 30.
  • 43
    • 33744826716 scopus 로고    scopus 로고
    • note
    • The hydride attack occurred from the opposite side of the bulky thiophenyl group at C-I, which occupies an axial position (shown below). The configuration of 42 was readily assigned by inspection of the 1,2-coupling constant.
  • 44
    • 0030506198 scopus 로고    scopus 로고
    • There are some reports on the synthesis of β-2-deoxyribonucleosides using the 1,3-anchimeric assistance, see: (a) Mukaiyama, T.; Uchiro, H.; Hirano, N.; Ichikawa, T. Chem. Lett. 1996, 629-630.
    • (1996) Chem. Lett. , pp. 629-630
    • Mukaiyama, T.1    Uchiro, H.2    Hirano, N.3    Ichikawa, T.4
  • 49
    • 0021997784 scopus 로고
    • Wiesner et al. reported the synthesis of β-2-deoxyglycosides by the anchimeric assistance of a N-methylurethane group and a 4-methoxybenzoyl group, see: Wiesner, K.; Tsai, T. Y. R.; Jin, H. Helv. Chim. Acta 1985. 68, 300-314.
    • (1985) Chim. Acta , vol.68 , pp. 300-314
    • Wiesner, K.1    Tsai, T.Y.R.2    Helv, J.H.3
  • 50
    • 84972955605 scopus 로고
    • However, Binkley et al. suggested that the anchimeric assistance from the C-3 position was not the dominating characteristic of glycosyl donors having an acyloxy group at the C-2 position, see: Binkley, R. W.; Koholic, D. J. J. Carbohydr. Chem. 1988, 7, 487-489.
    • (1988) J. Carbohydr. Chem. , vol.7 , pp. 487-489
    • Binkley, R.W.1    Koholic, D.J.2
  • 52
    • 33744819078 scopus 로고    scopus 로고
    • note
    • 2O, α-47b was preferentially obtained in 46% yield with 1:3 (β:α) selectivity.
  • 53
    • 33744811878 scopus 로고    scopus 로고
    • note
    • Interestingly, in the case of trichloroimidate 4b′ as a glycosyl donor, α-selective glycosidation proceeded to give 46b in 80% yield with 1:20 (β:α) selectivity.
  • 54
    • 33744787782 scopus 로고    scopus 로고
    • note
    • Synthetic sordarin was tested for fungal growth inhibition in C. albicans, C. glabrata, C. parapsilosis, and C. neoformans.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.