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Volumn 64, Issue 6, 1999, Pages 1932-1940

Total synthesis of (+)-himbacine and (+)-himbeline

Author keywords

[No Author keywords available]

Indexed keywords

HIMBACINE; HIMBELINE; ISOHIMBACINE; UNCLASSIFIED DRUG;

EID: 0033583274     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981983+     Document Type: Article
Times cited : (71)

References (53)
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    • (c) Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529. For X-ray crystallographic studies on himbacine see: Fridrichsons, J.; Mathieson, A. M. Acta Crystallogr. 1962, 15, 119.
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    • (c) Ritchie, E.; Taylor, W. C. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, p 529. For X-ray crystallographic studies on himbacine see: Fridrichsons, J.; Mathieson, A. M. Acta Crystallogr. 1962, 15, 119.
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    • note
    • (d) Himbacine was isolated from the bark of Galbulimima baccata which is a member of the magnolia family, and not a pine tree as stated earlier. See ref 5b, footnote 6.
  • 13
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    • (b) For another total synthesis of himbacine, see: Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023. For studies directed toward the total synthesis of himbacine, see:
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9369
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    • (b) For another total synthesis of himbacine, see: Hart, D. J.; Wu, W.-L.; Kozikowski, A. P. J. Am. Chem. Soc. 1995, 117, 9369. Also see: Hart, D. J.; Li, J.; Wu, W.-L.; Kozikowski, A. P. J. Org. Chem. 1997, 62, 5023. For studies directed toward the total synthesis of himbacine, see:
    • (1997) J. Org. Chem. , vol.62 , pp. 5023
    • Hart, D.J.1    Li, J.2    Wu, W.-L.3    Kozikowski, A.P.4
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    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 9190
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    • note
    • (S)-3-Butyn-2-ol was purchased from Chiroscience Ltd, Cambridge Science Park, Milton Rd, Cambridge CB4 4WE, England. It is also available from DSM Fine Chemicals, 217 Route 46 W, Saddle Brook, NJ 07663-6253.
  • 36
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  • 38
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    • note
    • 4a in comparison to compound 19.
  • 39
    • 0344922015 scopus 로고    scopus 로고
    • note
    • 9 double bond.
  • 40
    • 0345353369 scopus 로고    scopus 로고
    • note
    • Isohimbacine (1a) did not undergo isomerization to himbacine (1) under several attempted conditions.
  • 41
    • 0344922014 scopus 로고    scopus 로고
    • note
    • 4 proton by the piperidine nitrogen.
  • 43
    • 0344059730 scopus 로고    scopus 로고
    • note
    • The workup procedure involved addition of excess of ammonium hydroxide. This step converted the unreacted reagent, which coeluted with the product, to more polar tert-butyl urethane.
  • 46
    • 0344490952 scopus 로고    scopus 로고
    • note
    • The technical grade chromous chloride (95%) available from Aldrich was used. Chromous chloride of high purity (99.9%), purchased from Strem Chemicals, gave inferior yields.
  • 47
    • 0001071162 scopus 로고
    • Prolonged reaction time resulted in the formation of substantial amounts of N-deprotected free amine corresponding to 33, which could be readily converted to 33 by treatment of the crude reaction mixture with Boc anhydride in the presence of 20% aqueous sodium hydroxide. Thermolytic deprotection of the tert-butoxycarbonyl protecting group on indoles and pyrroles has been reported: Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 6141
    • Rawal, V.H.1    Cava, M.P.2
  • 48
    • 0345353368 scopus 로고    scopus 로고
    • note
    • A large excess (8-12 wt equiv) of Raney nickel was necessary. Commercially available (Aldrich) Raney nickel was washed as mentioned before (ref 17) prior to use.
  • 49
    • 0345353367 scopus 로고    scopus 로고
    • note
    • 3)].
  • 50
    • 0344922012 scopus 로고    scopus 로고
    • note
    • 3)].
  • 51
    • 0344922011 scopus 로고    scopus 로고
    • note
    • 3)].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.