메뉴 건너뛰기




Volumn 72, Issue 26, 2007, Pages 10065-10074

Efficient and stereoselective dimerization of pyrroloindolizine derivatives inspired by a hypothesis for the biosynthesis of complex myrmicarin alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

HETERODIMERIZATION REACTIONS; LEWIS ACIDS;

EID: 37549029806     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701981q     Document Type: Article
Times cited : (22)

References (31)
  • 8
    • 0001357443 scopus 로고
    • For FMO analysis of cycloadditions involving fulvenes, see: a
    • For FMO analysis of cycloadditions involving fulvenes, see: (a) Houk, K. N.; George, J. K.; Duke, R. E., Jr. Tetrahedron 1974, 30, 523-533.
    • (1974) Tetrahedron , vol.30 , pp. 523-533
    • Houk, K.N.1    George, J.K.2    Duke Jr., R.E.3
  • 12
    • 0037182748 scopus 로고    scopus 로고
    • For formal [6 + 2] cycloadditions involving fulvene species, see: (e) Hong, B.-C.; Shr, Y.-J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249-2252.
    • For formal [6 + 2] cycloadditions involving fulvene species, see: (e) Hong, B.-C.; Shr, Y.-J.; Wu, J.-L.; Gupta, A. K.; Lin, K.-J. Org. Lett. 2002, 4, 2249-2252.
  • 14
    • 2942566295 scopus 로고    scopus 로고
    • For a review on the chemistry of C-vinyl pyrrole derivatives, see: (a) Trofimov, B. A.; Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. I. Chem. Rev. 2004, 104, 2481-2506.
    • For a review on the chemistry of C-vinyl pyrrole derivatives, see: (a) Trofimov, B. A.; Sobenina, L. N.; Demenev, A. P.; Mikhaleva, A. I. Chem. Rev. 2004, 104, 2481-2506.
  • 15
    • 33748972144 scopus 로고    scopus 로고
    • In Five-Membered Ring Systems: Pyrroles and Benzo Derivatives; Gribble, G
    • For general reviews on the chemistry of pyrroles, see: b, Joule, J, Eds, Elsevier Ltd, Oxford, UK
    • For general reviews on the chemistry of pyrroles, see: (b) Pelkey, E. T. In Five-Membered Ring Systems: Pyrroles and Benzo Derivatives; Gribble, G., Joule, J., Eds.; Progress in Heterocyclic Chemistry, Vol. 17; Elsevier Ltd.: Oxford, UK, 2005; pp 109-141.
    • (2005) Progress in Heterocyclic Chemistry , vol.17 , pp. 109-141
    • Pelkey, E.T.1
  • 16
    • 0004267670 scopus 로고
    • Jones, A, Ed, Wiley: New York
    • (c) Jones, A., Ed. Pyrroles; Wiley: New York, 1990.
    • (1990) Pyrroles
  • 19
    • 37549047549 scopus 로고    scopus 로고
    • Heating a solution of this mixture of dimer 20 and sulfide 22 (55°C) resulted only in decomposition of the dimer.
    • Heating a solution of this mixture of dimer 20 and sulfide 22 (55°C) resulted only in decomposition of the dimer.
  • 20
    • 37549019270 scopus 로고    scopus 로고
    • DFT calculations performed using B3LYP/6-31G; gas phase, energy-minimized structure of the free azafulvenium ions.
    • DFT calculations performed using B3LYP/6-31G; gas phase, energy-minimized structure of the free azafulvenium ions.
  • 23
    • 37549000122 scopus 로고    scopus 로고
    • Attempts to introduce the C9-alcohol via the C8-C9 silyl enol ether by dihydroxylation or epoxidation failed, likely as a result of the sensitivity of the vinyl pyrrole nucleus toward oxidation.
    • Attempts to introduce the C9-alcohol via the C8-C9 silyl enol ether by dihydroxylation or epoxidation failed, likely as a result of the sensitivity of the vinyl pyrrole nucleus toward oxidation.
  • 24
    • 37549031672 scopus 로고    scopus 로고
    • The presence of a free C3-hydroxyl group significantly complicated the introduction of the C9-hydoxyl group.
    • The presence of a free C3-hydroxyl group significantly complicated the introduction of the C9-hydoxyl group.
  • 25
    • 0033518571 scopus 로고    scopus 로고
    • For the synthesis of E(O)- and Z(O)-thiolketene acetal 41, see: Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699
    • For the synthesis of E(O)- and Z(O)-thiolketene acetal 41, see: Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699
  • 27
    • 37549045594 scopus 로고    scopus 로고
    • Under the conditions described above, thiolester 42 was obtained as an inseparable mixture of diastereomers (dr, 1:17:2.5:13). Use of the corresponding Z-thiolketeneacetal (2.00 equiv, E(O):Z(O) = 1:12) gave 42 with a diminished level of diastereoselection (dr, 1:2.1:1.4:2.3).
    • Under the conditions described above, thiolester 42 was obtained as an inseparable mixture of diastereomers (dr, 1:17:2.5:13). Use of the corresponding Z-thiolketeneacetal (2.00 equiv, E(O):Z(O) = 1:12) gave 42 with a diminished level of diastereoselection (dr, 1:2.1:1.4:2.3).
  • 28
    • 37549013697 scopus 로고    scopus 로고
    • 1H NMR monitoring of the homogeneous reaction mixture showed complete consumption of 40 with concomitant formation of 43 and no other visible compounds except remaining excess 2.
    • 1H NMR monitoring of the homogeneous reaction mixture showed complete consumption of 40 with concomitant formation of 43 and no other visible compounds except remaining excess 2.
  • 30
    • 37549039034 scopus 로고    scopus 로고
    • 1H NMR monitoring of the homogeneous reaction mixture showed complete consumption of 47 and 2 with concomitant clean and exclusive formation of 49.
    • 1H NMR monitoring of the homogeneous reaction mixture showed complete consumption of 47 and 2 with concomitant clean and exclusive formation of 49.
  • 31
    • 37549055393 scopus 로고    scopus 로고
    • The oxidation of the more electron-rich pyrroloindolozine substructure is greatly accelerated in the presence of acid
    • The oxidation of the more electron-rich pyrroloindolozine substructure is greatly accelerated in the presence of acid.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.