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Volumn 10, Issue 19, 2008, Pages 4179-4182

Synthetic studies toward pectenotoxin 2. Part I. Stereocontrolled access to the C10-C22 fragment

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PECTENOTOXIN 2; PYRAN DERIVATIVE;

EID: 55449115385     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8015868     Document Type: Article
Times cited : (28)

References (47)
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    • For selected examples, see: (a) Japan: see ref 1, 2a,b
    • For selected examples, see: (a) Japan: see ref 1, 2a,b.
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    • Korea: Jung, J. H.; Sim, C. J.; Lee, C.-O. J. Nat. Prod. 1995, 58, 1722-1726.
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    • New Zealand and Norway: see ref 2d, d) Ireland: see ref 2c, e Finland: Kuuppo, P, Uronen, P, Petermann, A, Tamminen, T, Granéli, E. Limnol. Oceanogr. 2006, 51, 2300-2307
    • (c) New Zealand and Norway: see ref 2d. (d) Ireland: see ref 2c. (e) Finland: Kuuppo, P.; Uronen, P.; Petermann, A.; Tamminen, T.; Granéli, E. Limnol. Oceanogr. 2006, 51, 2300-2307.
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    • For total synthesis of PTX4 and PTX8, see: (a) Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4569-4573.
    • For total synthesis of PTX4 and PTX8, see: (a) Evans, D. A.; Rajapakse, H. A.; Stenkamp, D. Angew. Chem., Int. Ed. 2002, 41, 4569-4573.
  • 28
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    • For additions of organometallic reagents to ́-hydroxyketones, see: a
    • For additions of organometallic reagents to ́-hydroxyketones, see: (a) Ukaji, Y.; Kanda, H.; Yamamoto, K.; Fujisawa, T. Chem. Lett. 1990, 597-600.
    • (1990) Chem. Lett , pp. 597-600
    • Ukaji, Y.1    Kanda, H.2    Yamamoto, K.3    Fujisawa, T.4
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    • The entire synthetic sequence was successfully scaled up to ca. a 20 g scale
    • The entire synthetic sequence was successfully scaled up to ca. a 20 g scale.
  • 33
    • 55449096098 scopus 로고    scopus 로고
    • The stereochemistry of the aldol and the methyltitanation steps was established by extensive NOE studies of the CDE and CDEF ring systems. See the following paper in this issue: Helmboldt, H.; Aho, J. E.; Pihko, P. M. Org. Lett. 2008, 10, 4183-4185.
    • The stereochemistry of the aldol and the methyltitanation steps was established by extensive NOE studies of the CDE and CDEF ring systems. See the following paper in this issue: Helmboldt, H.; Aho, J. E.; Pihko, P. M. Org. Lett. 2008, 10, 4183-4185.
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    • For excellent discussions and predictions in both cyclic and acyclic systems, see
    • (a) Cornforth, J. W.; Cornforth, R. H.; Mathew, K. K. J. Chem. Soc. 1959, 11, 2-127. For excellent discussions and predictions in both cyclic and acyclic systems, see:
    • (1959) J. Chem. Soc , vol.11 , pp. 2-127
    • Cornforth, J.W.1    Cornforth, R.H.2    Mathew, K.K.3
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    • Evans, D. A.; Cee, V. J.; Siska, S. J. J. Am. Chem. Soc. 2006, 128, 9433-9441, and refs therein. The high level of diastereoselection observed suggests that the α,β relationship of the oxygen substituents in 3 represents a stereochemically reinforcing case. For a related highly selective aldol bond construction, see:
    • (b) Evans, D. A.; Cee, V. J.; Siska, S. J. J. Am. Chem. Soc. 2006, 128, 9433-9441, and refs therein. The high level of diastereoselection observed suggests that the α,β relationship of the oxygen substituents in 3 represents a stereochemically reinforcing case. For a related highly selective aldol bond construction, see:
  • 41
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    • See Supporting Information for further details
    • See Supporting Information for further details.
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    • There are two possible modes to achieve 1,3-induction in hydroxyl-directed additions: the nucleophile is delivered either externally (from an external reagent) or internally (directed addition): (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. A chelation-controlled transition state model has also been suggested,
    • There are two possible modes to achieve 1,3-induction in hydroxyl-directed additions: the nucleophile is delivered either externally (from an external reagent) or internally (directed addition): (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578. A chelation-controlled transition state model has also been suggested,
  • 43
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    • Chem. Soc, For a review, see
    • (b) Reetz, M. T.; Jung, A. J. Am. Chem. Soc. 1983, 105, 4833-4835. For a review, see:
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    • Reetz, M.T.1    Jung, A.2
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    • For further details, including screens for different solvents and additives, see Supporting Information
    • For further details, including screens for different solvents and additives, see Supporting Information.
  • 47
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    • Excess Ti(OiPr)4 should facilitate the removal of the product from the metal center and assist in the formation of an active complex
    • 4 should facilitate the removal of the product from the metal center and assist in the formation of an active complex: Wu, K.-H.; Gau, H.-M. Organometallics 2004, 23, 580-588.
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    • Wu, K.-H.1    Gau, H.-M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.