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Volumn 70, Issue 10, 2005, Pages 3898-3902

An N-acyliminium cyclization approach to a total synthesis of (+)-cylindricine C

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR STRUCTURE; PROBLEM SOLVING; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 18744409514     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0501846     Document Type: Article
Times cited : (48)

References (61)
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    • in press
    • For a detailed account on efforts involving the cylindricine synthesis, see: Liu, J.; Hsung, R. P. ChemTracts 2005, 18, in press.
    • (2005) ChemTracts , vol.18
    • Liu, J.1    Hsung, R.P.2
  • 5
    • 0000932594 scopus 로고    scopus 로고
    • For the first two total syntheses of (±)-cylindricines, see: (a) Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630.
    • (1997) J. Org. Chem. , vol.62 , pp. 5630
    • Snider, B.B.1    Liu, T.2
  • 7
    • 0344436088 scopus 로고    scopus 로고
    • For the total synthesis of (-)-cylindricines, see: (a) Molander, G. A.; Ronn, M. J. Org. Chem. 1999, 64, 5183.
    • (1999) J. Org. Chem. , vol.64 , pp. 5183
    • Molander, G.A.1    Ronn, M.2
  • 9
    • 0348041999 scopus 로고    scopus 로고
    • For recent syntheses of (+)-cylindricines, see: (a) Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599.
    • (2003) Org. Lett. , vol.5 , pp. 4599
    • Trost, B.M.1    Rudd, M.T.2
  • 11
    • 18744396201 scopus 로고    scopus 로고
    • See ref 17
    • (c) See ref 17.
  • 19
    • 0037241493 scopus 로고    scopus 로고
    • (a) For a detailed account on efforts involving the lepadiformine synthesis, see: (a) Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 59
    • Weinreb, S.M.1
  • 28
    • 18744377330 scopus 로고    scopus 로고
    • See ref 17
    • (d) See ref 17.
  • 29
    • 0037077015 scopus 로고    scopus 로고
    • For a recent total synthesis of (-)-lepadiformine, see: (a) Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337.
    • (2002) J. Org. Chem. , vol.67 , pp. 4337
    • Sun, P.1    Sun, C.2    Weinreb, S.M.3
  • 31
    • 0035515394 scopus 로고    scopus 로고
    • For a recent total synthesis of (±)-lepadiformine, see: Greshock, T. J.; Funk, R. L. Org. Lett. 2001, 3, 3511.
    • (2001) Org. Lett. , vol.3 , pp. 3511
    • Greshock, T.J.1    Funk, R.L.2
  • 33
    • 0000564844 scopus 로고
    • For some examples of natural product synthesis that employ tandem Mannich strategy, see: (a) Corey, E. J.; Balanson, R. D. J. Am. Chem Soc. 1974, 96, 6516.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 6516
    • Corey, E.J.1    Balanson, R.D.2
  • 40
    • 13444249603 scopus 로고    scopus 로고
    • For a recent account employing a similar concept of achieving total syntheses of both (-)-lepadiformine and (+)-cylindricines C-E via a aza-spirocyclic common intermediate, see: Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2005, 127, 1473.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1473
    • Abe, H.1    Aoyagi, S.2    Kibayashi, C.3
  • 42
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    • Brossi, A., Ed.; Academic Press: San Diego, CA
    • (a) For a related review, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Brossi, A., Ed.; Academic Press: San Diego, CA, 1988; Vol. 2, pp 271-339.
    • (1988) Comprehensive Organic Synthesis , vol.2 , pp. 271-339
    • Hiemstra, H.1    Speckamp, W.N.2
  • 53
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    • note
    • The use of alkenes for the aza-Prins-type N-acyliminium addition in this case also failed. Please refer to ref 6c for numerous examples of addition of alkenes to N-acyliminium (diagram presented)
  • 54
    • 18744409200 scopus 로고    scopus 로고
    • note
    • Kibayashi also reported similar difficulties with alkenes and unsubstituted dienes: see ref 17.
  • 55
    • 18744412762 scopus 로고    scopus 로고
    • note
    • 2O quenching instead of the desired the γ-proton.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.