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Volumn 74, Issue 3, 2009, Pages 1205-1211

Enantioselective formal synthesis of (+)-dihydrocorynantheine and (-)-dihydrocorynantheol

Author keywords

[No Author keywords available]

Indexed keywords

AUXILIARY GROUPS; CARBONYL GROUPS; CYCLO CONDENSATIONS; ENANTIOSELECTIVE; ENANTIOSELECTIVE CONSTRUCTIONS; FORMAL SYNTHESIS; INDOLE ALKALOIDS; OXINDOLE ALKALOIDS; STEREO-SELECTIVE; STEREOSELECTIVE CYCLIZATION; SUBSTITUTION PATTERNS; TOTAL SYNTHESIS;

EID: 64549158972     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802387c     Document Type: Article
Times cited : (48)

References (42)
  • 1
    • 64549141563 scopus 로고    scopus 로고
    • Brown, R. T. Indoles. The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; 25, Part 4, Chapter 3.
    • (a) Brown, R. T. Indoles. The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, Chapter 3.
  • 3
    • 64549129126 scopus 로고    scopus 로고
    • Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, UK, 1994; 25, Part 4, Chapter 3.
    • (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, UK, 1994; Vol. 25, Part 4, Chapter 3.
  • 5
    • 0025992651 scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
    • (1991) Tetrahedron , vol.47 , pp. 9503
    • Romo, D.1    Meyers, A.I.2
  • 18
    • 0034625424 scopus 로고    scopus 로고
    • For recent reviews on the chemistry of N-acyliminium ions, see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
    • For recent reviews on the chemistry of N-acyliminium ions, see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
  • 20
    • 0022408702 scopus 로고
    • For the use of this procedure in the synthesis of tetrahydro-β- carbolines, see
    • For the use of this procedure in the synthesis of tetrahydro-β- carbolines, see: Ishida, A.; Nakamura, T.; Irie, K.; Oh-Ishi, T. Chem. Pharm. Bull. 1985, 33, 3237.
    • (1985) Chem. Pharm. Bull , vol.33 , pp. 3237
    • Ishida, A.1    Nakamura, T.2    Irie, K.3    Oh-Ishi, T.4
  • 29
    • 64549102939 scopus 로고    scopus 로고
    • 13C NMR data of 15 were identical with those reported in the racemic series: Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M. Tetrahedron 1999, 45, 2692.
    • 13C NMR data of 15 were identical with those reported in the racemic series: Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M. Tetrahedron 1999, 45, 2692.
  • 30
    • 0030602267 scopus 로고    scopus 로고
    • 10b were identical with those reported in the racemic series: (a) Lounasmaa, M.; Hanhinen, P. Tetrahedron 1996, 52, 15225.
    • 10b were identical with those reported in the racemic series: (a) Lounasmaa, M.; Hanhinen, P. Tetrahedron 1996, 52, 15225.
  • 36
    • 85008129445 scopus 로고
    • For previous syntheses of, )-dihydrocorynantheol, see: a
    • For previous syntheses of (-)-dihydrocorynantheol, see: (a) Suzuki, T.; Sato, E.; Unno, K.; Kametani, T. Chem. Pharm. Bull. 1986, 34, 1584.
    • (1986) Chem. Pharm. Bull , vol.34 , pp. 1584
    • Suzuki, T.1    Sato, E.2    Unno, K.3    Kametani, T.4
  • 42
    • 33947474300 scopus 로고
    • For the conversion of, )-dihydrocorynantheine to, )-rhynchophylline and, -isorhynchophylline, see
    • For the conversion of (-)-dihydrocorynantheine to (-)-rhynchophylline and (+)-isorhynchophylline, see: Finch, N.; Taylor, W. I. J. Am. Chem. Soc. 1962, 84, 3871.
    • (1962) J. Am. Chem. Soc , vol.84 , pp. 3871
    • Finch, N.1    Taylor, W.I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.