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Volumn 8, Issue 4, 2006, Pages 777-780

A concise total synthesis of (-)-cylindricine C through a stereoselective intramolecular aza-[3 + 3] annulation strategy

Author keywords

[No Author keywords available]

Indexed keywords

CYLINDRICINE C; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; QUINOLONE DERIVATIVE;

EID: 33644746072     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053059p     Document Type: Article
Times cited : (51)

References (60)
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    • (d) For a recent account on total syntheses of both (-)-lepadiformine and (+)-cylindricines C-E via an aza-spirocyclic common intermediate, see: Abe, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 2005, 127, 1473.
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    • (a) For a detailed account on efforts involving the lepadiformine synthesis, see: (a) Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59.
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    • For total syntheses of fasicularin, see: (a) Maeng, J.-H, Funk, R. L. Org. Lett. 2002, 4, 331.
    • (2002) Org. Lett. , vol.4 , pp. 331
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    • For 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
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    • For total syntheses 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
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    • For a recent synthesis of (+)-cylindricines, see: (c) 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
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    • Also see 6d.
    • (e) Also see 6d.
  • 30
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    • For total syntheses of both (+)-cylindricines and (-)-lepadiformine via a common aza-tricyclic intermediate, see: (a) Liu, J.; Hsung, R. P.; Peters, S. D. Org. Lett. 2004, 6, 3989.
    • (2004) Org. Lett. , vol.6 , pp. 3989
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    • Enaminones as synthons
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    • For a review on vinylogous amide chemistry, see: Kucklander, U. Enaminones as Synthons. In The Chemistry of Functional Groups: The Chemistry of Enamines; Rappoport, Z., Ed.; John Wiley & Sons: New York, 1994; Part I, p 523.
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    • Kucklander, U.1
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    • note
    • See the Supporting Information.
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    • note
    • Although we did not rigorously assign the relative stereochemistry at C4 and C5, we believed that NCS should have approached from the less hindered bottom face as observed in the hydrogenation of 27 that gave i in 90% yield as a single diastereomer. The relative stereochemistry C4 and C5 is unambiguous on the basis of coupling constants obtained for H4a and H4b. (Diagram presented)
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    • note
    • The deprotection was carried out earlier than expected because we could not do anything with 33 in completing the total synthesis.
  • 54
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    • note
    • 8.
  • 58
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    • For some recent examples, see: (a) Ginn, J. D.; Padwa, A. Org. Lett. 2002, 4, 1515.
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    • note
    • 2) (see ref 10b).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.