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Volumn 6, Issue 6, 2004, Pages 977-980

First total synthesis of trans- and cis-resorcylide: Remarkable hydrogen-bond-controlled, stereospecific ring-closing metathesis

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; BENZYL CHLORIDE; HYDROGEN; MACROLIDE; RESORCYLIDE; UNCLASSIFIED DRUG;

EID: 1642569116     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400037     Document Type: Article
Times cited : (52)

References (42)
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    • Application of RCM in the synthesis of: (a) Zearalenone and lasiodiplodin: Fürstner, A.; Thiel, O. R.; Kindler, N.; Bartkowska, B. J. Org. Chem. 2000, 65, 7990. (b) Radicicol: Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903. (c) Salicylihalamides: (i) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (ii) Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (iii) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (iv) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (d) Oximidine II: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040.
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    • For recent reviews on RCM, see: (a) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (d) Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 2826.
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    • For recent reviews on RCM, see: (a) Maier, M. E. Angew. Chem., Int. Ed. 2000, 39, 2073. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (d) Prunet, J. Angew. Chem., Int. Ed. 2003, 42, 2826.
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    • note
    • Previous H-bond influence on RCM has been observed (see ref 7c,i).
  • 31
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    • note
    • Inversion of configuration was ensured by hydrolysis of ester 11 under basic conditions (aq NaOH (30%), DMSO, 70°C, 24 h, 60%) and measurement of the optical rotation power of the resulting alcohol.
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    • note
    • The bromide originally designed is readily converted to the corresponding phthalide. The observed reactivity of the alternatively used benzyl chlorides 11 and 15 under Stille conditions is impressive and unprecedented.
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    • Presence of an electron-deficient double bond directly suggests this catalyst selection. For related examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449. (b) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (c) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
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    • Presence of an electron-deficient double bond directly suggests this catalyst selection. For related examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449. (b) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (c) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
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    • Presence of an electron-deficient double bond directly suggests this catalyst selection. For related examples, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449. (b) Fürstner, A.; Thiel, O. R.; Ackermann, L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204. (c) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
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    • and references therein
    • Lee, C. W.; Grubbs, R. H. Org. Lett. 2000, 2, 2145 and references therein.
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    • note
    • 3).
  • 41
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    • note
    • Attempted deacetylation of 17 was also troublesome because of the formation of isocoumarins.


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