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Volumn 126, Issue 50, 2004, Pages 16553-16558

Total synthesis of (-)-incarvilline, (+)-incarvine C, and (-)-incarvillateine

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; DERIVATIVES; DIMERIZATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 11444268894     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0401702     Document Type: Article
Times cited : (108)

References (33)
  • 10
    • 0017078239 scopus 로고
    • Compound 9 was prepared via TBDMS protection (Tanaka, T.; Kurozumi, S.; Toru, T.; Miura, S.; Kobayashi, M.; Ishimoto, S. Tetrahedron 1976, 32, 1713-1718) of 4(S)-hydroxycyclopent-2-enone. For the preparation of the latter compound, see: (a) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1976, 759-762. (b) Khanapure, S. P.; Najafi, N.; Manna, S.; Yang, J.-J.; Rokach, J. J. Org. Chem. 1995, 60, 7548-7551.
    • (1976) Tetrahedron , vol.32 , pp. 1713-1718
    • Tanaka, T.1    Kurozumi, S.2    Toru, T.3    Miura, S.4    Kobayashi, M.5    Ishimoto, S.6
  • 11
    • 0000901887 scopus 로고
    • Compound 9 was prepared via TBDMS protection (Tanaka, T.; Kurozumi, S.; Toru, T.; Miura, S.; Kobayashi, M.; Ishimoto, S. Tetrahedron 1976, 32, 1713-1718) of 4(S)-hydroxycyclopent-2-enone. For the preparation of the latter compound, see: (a) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1976, 759-762. (b) Khanapure, S. P.; Najafi, N.; Manna, S.; Yang, J.-J.; Rokach, J. J. Org. Chem. 1995, 60, 7548-7551.
    • (1976) Tetrahedron Lett. , pp. 759-762
    • Ogura, K.1    Yamashita, M.2    Tsuchihashi, G.3
  • 12
    • 0028856904 scopus 로고
    • Compound 9 was prepared via TBDMS protection (Tanaka, T.; Kurozumi, S.; Toru, T.; Miura, S.; Kobayashi, M.; Ishimoto, S. Tetrahedron 1976, 32, 1713-1718) of 4(S)-hydroxycyclopent-2-enone. For the preparation of the latter compound, see: (a) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1976, 759-762. (b) Khanapure, S. P.; Najafi, N.; Manna, S.; Yang, J.-J.; Rokach, J. J. Org. Chem. 1995, 60, 7548-7551.
    • (1995) J. Org. Chem. , vol.60 , pp. 7548-7551
    • Khanapure, S.P.1    Najafi, N.2    Manna, S.3    Yang, J.-J.4    Rokach, J.5
  • 13
    • 11444258401 scopus 로고    scopus 로고
    • note
    • This process involving elimination of the siloxy group seems unusual because there are some cases on trifluoroacetic acid-mediated Boc removal without concomitant loss of a silyl protecting group from an alcohol. As suggested by a referee, the elimination process in this case may be explained by a mechanism via an enol intermediate.
  • 14
    • 0037458985 scopus 로고    scopus 로고
    • For the construction of the 2-pyrindine ring system, see: (a) Hattori, K.; Grossman, R. B. J. Org. Chem. 2003, 68, 1409-1417. (b) Hong, B.-C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H.; Lee, G.-H. Org. Lett. 2003, 5, 1689-1692.
    • (2003) J. Org. Chem. , vol.68 , pp. 1409-1417
    • Hattori, K.1    Grossman, R.B.2
  • 15
    • 0141741220 scopus 로고    scopus 로고
    • For the construction of the 2-pyrindine ring system, see: (a) Hattori, K.; Grossman, R. B. J. Org. Chem. 2003, 68, 1409-1417. (b) Hong, B.-C.; Gupta, A. K.; Wu, M.-F.; Liao, J.-H.; Lee, G.-H. Org. Lett. 2003, 5, 1689-1692.
    • (2003) Org. Lett. , vol.5 , pp. 1689-1692
    • Hong, B.-C.1    Gupta, A.K.2    Wu, M.-F.3    Liao, J.-H.4    Lee, G.-H.5
  • 27
    • 84943076505 scopus 로고
    • For reviews on photodimerization in the solid state, see: (a) Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647-678.
    • (1971) Pure Appl. Chem. , vol.27 , pp. 647-678
    • Schmidt, G.M.J.1
  • 31
    • 11444254673 scopus 로고    scopus 로고
    • note
    • When the photoreaction was carried out by irradiating aqueous suspensions of the ferulate derivatives 34, the esters were found to be partly hydrolyzed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.