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Volumn 73, Issue 22, 2008, Pages 9033-9039

A new acyl radical-based route to the 1,5-methanoazocino[4,3-b]indole framework of uleine and strychnos alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

ACYL RADICALS; CHEMICAL EQUATIONS; CYCLIZATIONS; SUB STRUCTURES; TETRAHYDROPYRIDINES;

EID: 56449129891     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801998h     Document Type: Article
Times cited : (38)

References (50)
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    • For a review on the chemistry of acyl radicals, see: a
    • For a review on the chemistry of acyl radicals, see: (a) Chatgilialoglu, C.; Crich, D.; Komatsu, M.; Ryu, I. Chem. Rev. 1999, 99, 1991-2069.
    • (1999) Chem. Rev , vol.99 , pp. 1991-2069
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  • 8
    • 56449119677 scopus 로고    scopus 로고
    • For reviews, see: (a) Joule, J. A. In Indoles. The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed.; The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; 25, Part 4, Ch 6.
    • For reviews, see: (a) Joule, J. A. In Indoles. The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed.; The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, Ch 6.
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    • Alvarez, M.; Joule, J. A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.;Wiley: Chichester, 1994; Supplement to 25, Part 4, Ch 6.
    • (b) Alvarez, M.; Joule, J. A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.;Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Ch 6.
  • 10
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    • Cordell, G. A, Ed, Academic Press: New York, Ch 4
    • (c) Alvarez, M.; Joule, J. A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2001; Vol. 57, Ch 4.
    • (2001) The Alkaloids , vol.57
    • Alvarez, M.1    Joule, J.A.2
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    • Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; The Chemistry of Heterocylic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to 25, Part 4, Ch 7.
    • (b) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; The Chemistry of Heterocylic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Ch 7.
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    • Cordell, G. A, Ed, Academic Press: New York
    • (c) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1996; Vol. 48, pp 75-189.
    • (1996) The Alkaloids , vol.48 , pp. 75-189
    • Bosch, J.1    Bonjoch, J.2    Amat, M.3
  • 17
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    • For a leading review on the synthesis of nitrogen heterocycles by radical cyclization, see
    • For a leading review on the synthesis of nitrogen heterocycles by radical cyclization, see: Bowman, W. R.; Fletcher, A. J.; Potts, G. B. S. J. Chem. Soc., Perkin Trans. 1 2002, 2747-2762.
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 2747-2762
    • Bowman, W.R.1    Fletcher, A.J.2    Potts, G.B.S.3
  • 18
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    • For relevant radical cyclizations leading to bridged nitrogen heterocycles, see: a
    • For relevant radical cyclizations leading to bridged nitrogen heterocycles, see: (a) Della, E. W.; Knill, A. M. J. Org. Chem. 1996, 61, 7529-7533.
    • (1996) J. Org. Chem , vol.61 , pp. 7529-7533
    • Della, E.W.1    Knill, A.M.2
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    • See also ref 6
    • (n) See also ref 6.
  • 32
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    • For a preliminary report of this part of the work, see
    • For a preliminary report of this part of the work, see: Bennasar, M.-L.; Roca, T.; García-Díaz, D. Synlett 2008, 1487-1490.
    • (2008) Synlett , pp. 1487-1490
    • Bennasar, M.-L.1    Roca, T.2    García-Díaz, D.3
  • 33
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    • All attempts to carry out the amination-imine allylation sequence from an indole-3-carbaldehyde already incorporating a carboxylic ester at the 2-position resulted in lactamization
    • All attempts to carry out the amination-imine allylation sequence from an indole-3-carbaldehyde already incorporating a carboxylic ester at the 2-position resulted in lactamization.
  • 39
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    • Prepared from 2-ethylallyl methanesulfonate: (a) Plamondon, L.; Wuest, J. D. J. Org. Chem. 1991, 56, 2066-75, See Supporting Information.
    • Prepared from 2-ethylallyl methanesulfonate: (a) Plamondon, L.; Wuest, J. D. J. Org. Chem. 1991, 56, 2066-75, See Supporting Information.
  • 40
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    • See Supporting Information for details
    • See Supporting Information for details.
  • 45
  • 49
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    • For a recent review discussing RCM of amine-containing dienes, see
    • For a recent review discussing RCM of amine-containing dienes, see: Compain, P. Adv. Synth. Catal. 2007, 349, 1829-1846.
    • (2007) Adv. Synth. Catal , vol.349 , pp. 1829-1846
    • Compain, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.