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Volumn 125, Issue 34, 2003, Pages 10238-10240

Construction of eight-membered ether rings by olefin geometry-dependent internal alkylation: First asymmetric total syntheses of (+)-3-(E)- and (+)-3-(Z)-pinnatifidenyne

Author keywords

[No Author keywords available]

Indexed keywords

KETONES; OLEFINS; SYNTHESIS (CHEMICAL);

EID: 0042931243     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035538u     Document Type: Article
Times cited : (62)

References (46)
  • 3
    • 0034142130 scopus 로고    scopus 로고
    • and earlier reviews in the same series
    • (c) Faulkner, D. J. Nat. Prod. Rep. 2000, 17, 1-6 and earlier reviews in the same series.
    • (2000) J. Nat. Prod. Rep. , vol.17 , pp. 1-6
    • Faulkner, D.1
  • 6
    • 0000330557 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Mehta, G.; Singh, V. Chem. Rev. 1999, 99, 881-930.
    • (1999) Chem. Rev. , vol.99 , pp. 881-930
    • Mehta, G.1    Singh, V.2
  • 7
    • 0034246704 scopus 로고    scopus 로고
    • (b) Yet, L. Chem. Rev. 2000, 100, 2963-3007.
    • (2000) Chem. Rev. , vol.100 , pp. 2963-3007
    • Yet, L.1
  • 9
    • 0034647232 scopus 로고    scopus 로고
    • and references therein
    • For a recent example of the total synthesis of natural products with eight-membered ether rings, see: (d) Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473-5476 and references therein. (e) Boeckman, R. K., Jr.; Jhang, J.; Reeder, M. R. Org. Lett. 2002, 4, 3891-3894. (f) Saitoh, T.; Suzuki, T.; Sugimoto, M.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2003, 44, 3175-3178.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 5473-5476
    • Crimmins, M.T.1    Tabet, E.A.2
  • 10
    • 0038003761 scopus 로고    scopus 로고
    • For a recent example of the total synthesis of natural products with eight-membered ether rings, see: (d) Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473-5476 and references therein. (e) Boeckman, R. K., Jr.; Jhang, J.; Reeder, M. R. Org. Lett. 2002, 4, 3891-3894. (f) Saitoh, T.; Suzuki, T.; Sugimoto, M.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2003, 44, 3175-3178.
    • (2002) Org. Lett. , vol.4 , pp. 3891-3894
    • Boeckman R.K., Jr.1    Jhang, J.2    Reeder, M.R.3
  • 11
    • 0037424749 scopus 로고    scopus 로고
    • For a recent example of the total synthesis of natural products with eight-membered ether rings, see: (d) Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473-5476 and references therein. (e) Boeckman, R. K., Jr.; Jhang, J.; Reeder, M. R. Org. Lett. 2002, 4, 3891-3894. (f) Saitoh, T.; Suzuki, T.; Sugimoto, M.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2003, 44, 3175-3178.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 3175-3178
    • Saitoh, T.1    Suzuki, T.2    Sugimoto, M.3    Hagiwara, H.4    Hoshi, T.5
  • 12
    • 0042907005 scopus 로고
    • M.S. Thesis, Seoul National University
    • Choi, W. J. M.S. Thesis, Seoul National University, 1995.
    • (1995)
    • Choi, W.J.1
  • 13
    • 0041403846 scopus 로고    scopus 로고
    • note
    • 3P.
  • 17
    • 0034549491 scopus 로고    scopus 로고
    • (b) Prepared from commercially available divinyl carbinol via modified Sharpless asymmetric epoxidation using cumene hydroperoxide instead of tert-butylhydroperoxide, see: Romero, A.; Wong, C. H. J. Org. Chem. 2000, 65, 8264-8268.
    • (2000) J. Org. Chem. , vol.65 , pp. 8264-8268
    • Romero, A.1    Wong, C.H.2
  • 18
    • 0042406194 scopus 로고    scopus 로고
    • note
    • 1H NMR of the corresponding Mosher esters.
  • 39
    • 0037116417 scopus 로고    scopus 로고
    • 16b recently isolated marine natural products. However. the spectral data of our synthetic material are distinctively different from those of the natural products. Professsor V. Roussis (University of Athens, Greece) is currently reinvestigating their structural assignment. See the Supporting Information. (a) Iliopoulou, D.; Vagias, C.; Harvala, C.; Roussis, V. Phytochemistry 2002, 59, 111-116. (b) San-Martin, A.; Darias, J.; Soto, H.; Contreras, J. S.; Rovirosa, J. Nat. Prod. Lett. 1997, 10, 303-311.
    • (2002) Phytochemistry , vol.59 , pp. 111-116
    • Iliopoulou, D.1    Vagias, C.2    Harvala, C.3    Roussis, V.4
  • 40
    • 0030669065 scopus 로고    scopus 로고
    • 16b recently isolated marine natural products. However. the spectral data of our synthetic material are distinctively different from those of the natural products. Professsor V. Roussis (University of Athens, Greece) is currently reinvestigating their structural assignment. See the Supporting Information. (a) Iliopoulou, D.; Vagias, C.; Harvala, C.; Roussis, V. Phytochemistry 2002, 59, 111-116. (b) San-Martin, A.; Darias, J.; Soto, H.; Contreras, J. S.; Rovirosa, J. Nat. Prod. Lett. 1997, 10, 303-311.
    • (1997) Nat. Prod. Lett. , vol.10 , pp. 303-311
    • San-Martin, A.1    Darias, J.2    Soto, H.3    Contreras, J.S.4    Rovirosa, J.5
  • 46
    • 0042406193 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.