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Volumn 68, Issue 16, 2003, Pages 6360-6368

Preparation and cycloaddition reactions of enantiopure 2-(N-acylamino)-1,3-dienes for the synthesis of octahydroquinoline derivatives

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; DERIVATIVES; SYNTHESIS (CHEMICAL);

EID: 0043076452     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0344687     Document Type: Article
Times cited : (63)

References (44)
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    • A similar approach to the synthesis of enantiopure octahydroquinolines is based on Diels-Alder reactions of N-acyl 5-vinyl-2,3-dihydro-4-pyridones prepared by Stille coupling reaction of the corresponding 5-iodo substituted pyridones with tributyl(vinyl)tin. Kuethe, J. T.; Brooks, C. A.; Comins, D. L. Org. Lett. 2003, 5, 321-323.
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    • The importance of these compounds arises from the presence of the decahydroquinoline ring in several natural alkaloids isolated from, e.g., the tunicate Clavelina lepadiformis, predatory flatworm Prostheceraeus villatus, Lycopodium club mosses, skin of Dendrobates amphibians, and myrmicine ants. These and several, related synthetic molecules exert diverse biological activities which depend on the type and degree of substitution and ring fusion. See, for example: Spande, T. F.; Jain, P.; Garraffo, H. M.; Pannell, L. K.; Yeh, H. J. C.; Daly, J. W.; Fukumoto, S.; Imamura, K.; Tokuyama, T.; Torres, J. A.; Snelling, R. R.; Jones, T. H. J. Nat. Prod. 1999, 62, 5-21. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169. Ozawa, T.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347 and referenced therein. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201 and references therein.
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    • Spande, T.F.1    Jain, P.2    Garraffo, H.M.3    Pannell, L.K.4    Yeh, H.J.C.5    Daly, J.W.6    Fukumoto, S.7    Imamura, K.8    Tokuyama, T.9    Torres, J.A.10    Snelling, R.R.11    Jones, T.H.12
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    • The importance of these compounds arises from the presence of the decahydroquinoline ring in several natural alkaloids isolated from, e.g., the tunicate Clavelina lepadiformis, predatory flatworm Prostheceraeus villatus, Lycopodium club mosses, skin of Dendrobates amphibians, and myrmicine ants. These and several, related synthetic molecules exert diverse biological activities which depend on the type and degree of substitution and ring fusion. See, for example: Spande, T. F.; Jain, P.; Garraffo, H. M.; Pannell, L. K.; Yeh, H. J. C.; Daly, J. W.; Fukumoto, S.; Imamura, K.; Tokuyama, T.; Torres, J. A.; Snelling, R. R.; Jones, T. H. J. Nat. Prod. 1999, 62, 5-21. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169. Ozawa, T.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347 and referenced therein. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201 and references therein.
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    • Cordell, G. A., Ed.; Academic Press: New York
    • The importance of these compounds arises from the presence of the decahydroquinoline ring in several natural alkaloids isolated from, e.g., the tunicate Clavelina lepadiformis, predatory flatworm Prostheceraeus villatus, Lycopodium club mosses, skin of Dendrobates amphibians, and myrmicine ants. These and several, related synthetic molecules exert diverse biological activities which depend on the type and degree of substitution and ring fusion. See, for example: Spande, T. F.; Jain, P.; Garraffo, H. M.; Pannell, L. K.; Yeh, H. J. C.; Daly, J. W.; Fukumoto, S.; Imamura, K.; Tokuyama, T.; Torres, J. A.; Snelling, R. R.; Jones, T. H. J. Nat. Prod. 1999, 62, 5-21. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169. Ozawa, T.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347 and referenced therein. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201 and references therein.
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    • and referenced therein
    • The importance of these compounds arises from the presence of the decahydroquinoline ring in several natural alkaloids isolated from, e.g., the tunicate Clavelina lepadiformis, predatory flatworm Prostheceraeus villatus, Lycopodium club mosses, skin of Dendrobates amphibians, and myrmicine ants. These and several, related synthetic molecules exert diverse biological activities which depend on the type and degree of substitution and ring fusion. See, for example: Spande, T. F.; Jain, P.; Garraffo, H. M.; Pannell, L. K.; Yeh, H. J. C.; Daly, J. W.; Fukumoto, S.; Imamura, K.; Tokuyama, T.; Torres, J. A.; Snelling, R. R.; Jones, T. H. J. Nat. Prod. 1999, 62, 5-21. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169. Ozawa, T.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347 and referenced therein. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201 and references therein.
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    • and references therein
    • The importance of these compounds arises from the presence of the decahydroquinoline ring in several natural alkaloids isolated from, e.g., the tunicate Clavelina lepadiformis, predatory flatworm Prostheceraeus villatus, Lycopodium club mosses, skin of Dendrobates amphibians, and myrmicine ants. These and several, related synthetic molecules exert diverse biological activities which depend on the type and degree of substitution and ring fusion. See, for example: Spande, T. F.; Jain, P.; Garraffo, H. M.; Pannell, L. K.; Yeh, H. J. C.; Daly, J. W.; Fukumoto, S.; Imamura, K.; Tokuyama, T.; Torres, J. A.; Snelling, R. R.; Jones, T. H. J. Nat. Prod. 1999, 62, 5-21. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169. Ozawa, T.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 2001, 66, 3338-3347 and referenced therein. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201 and references therein.
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    • This should increase the rate of the transmetalation step. Molander has recently reported on the use of potassium vinyltrifluoroborate as a useful reagent for introducing a vinyl moiety by Pd-catalyzed reaction with aryl halides and triflates without competing Heck reaction. Molander, G. A.; Rivero, M. R. Org. Lett. 2002, 4, 107-109.
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    • note
    • The X-ray CIF files for all structures have been deposited at the Cambridge Crystallographic Data Centre and allocated with the deposition numbers CCDC 200006 for compound 15a, CCDC 200008 for compound 15b, CCDC 200007 for compound 15c, CCDC 201406 for compound 20b, CCDC 208282 for 21d.
  • 36
    • 0043230370 scopus 로고    scopus 로고
    • note
    • A Monte Carlo conformational search did not rule out, however, other possible conformations stabilized by π-stacking between the phenyl group of the auxiliary and the external double bond, which further complicate the interpretation of the stereochemical outcome.
  • 37
    • 0043230371 scopus 로고    scopus 로고
    • note
    • STO 3-21G* ab initio calculations allowed us to predict, for the reaction of dienes 10a-c with ethyl acrylate, the formation of the 6-substituted products according to HOMO diene-LUMO dienophile interactions. In the case of 10b, the exact ratio between the four major diastereomers was 2.3:2:1.2:1.
  • 38
    • 0041727839 scopus 로고    scopus 로고
    • note
    • 1H NMR) of the crude reaction mixture.
  • 39
    • 0042729122 scopus 로고    scopus 로고
    • note
    • H-7 couples with only one proton on C-6 (which excludes the 5-regioisomer), with a J = 6.8 Hz very close to that between the same protons in 20b (6.3 Hz).
  • 40
    • 0041727838 scopus 로고    scopus 로고
    • note
    • The reasons behind this stereochemical result have to be sought in the interaction between the two chiral residues and the n-butyl chain in the transition state of the process, although it is difficult at the present to suggest a model. It is interesting to observe that a similar "upper face" approach was prevailing in the formation of the exo product 19 in the reaction of N-phenylmaleimide with n-butyl substituted diene 13b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.