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Total synthesis of (+/−)-frondosin B and (+/−)-5-epi-liphagal by using a concise (4+3) cycloaddition approach

Duchan Laplace (UGent) , Bart Verbraeken (UGent) , Kristof Van Hecke (UGent) and Johan Winne (UGent)
(2014) CHEMISTRY-A EUROPEAN JOURNAL. 20(1). p.253-262
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Abstract
A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl-type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven-membered rings.
Keywords
LIPHAGAL, SYSTEMS, SKELETONS, DERIVATIVES, (-)-FRONDOSIN-B, (+/-)-FRONDOSIN-B, INHIBITOR, FRONDOSIN-B, ENANTIOSELECTIVE TOTAL-SYNTHESIS, cycloheptanes, cycloaddition reactions, furans, natural products, total synthesis

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Citation

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MLA
Laplace, Duchan, et al. “Total Synthesis of (+/−)-Frondosin B and (+/−)-5-Epi-Liphagal by Using a Concise (4+3) Cycloaddition Approach.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 20, no. 1, 2014, pp. 253–62.
APA
Laplace, D., Verbraeken, B., Van Hecke, K., & Winne, J. (2014). Total synthesis of (+/−)-frondosin B and (+/−)-5-epi-liphagal by using a concise (4+3) cycloaddition approach. CHEMISTRY-A EUROPEAN JOURNAL, 20(1), 253–262.
Chicago author-date
Laplace, Duchan, Bart Verbraeken, Kristof Van Hecke, and Johan Winne. 2014. “Total Synthesis of (+/−)-Frondosin B and (+/−)-5-Epi-Liphagal by Using a Concise (4+3) Cycloaddition Approach.” CHEMISTRY-A EUROPEAN JOURNAL 20 (1): 253–62.
Chicago author-date (all authors)
Laplace, Duchan, Bart Verbraeken, Kristof Van Hecke, and Johan Winne. 2014. “Total Synthesis of (+/−)-Frondosin B and (+/−)-5-Epi-Liphagal by Using a Concise (4+3) Cycloaddition Approach.” CHEMISTRY-A EUROPEAN JOURNAL 20 (1): 253–262.
Vancouver
1.
Laplace D, Verbraeken B, Van Hecke K, Winne J. Total synthesis of (+/−)-frondosin B and (+/−)-5-epi-liphagal by using a concise (4+3) cycloaddition approach. CHEMISTRY-A EUROPEAN JOURNAL. 2014;20(1):253–62.
IEEE
[1]
D. Laplace, B. Verbraeken, K. Van Hecke, and J. Winne, “Total synthesis of (+/−)-frondosin B and (+/−)-5-epi-liphagal by using a concise (4+3) cycloaddition approach,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 20, no. 1, pp. 253–262, 2014.
@article{4378437,
  abstract     = {A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl-type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven-membered rings.},
  author       = {Laplace, Duchan and Verbraeken, Bart and Van Hecke, Kristof and Winne, Johan},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {LIPHAGAL,SYSTEMS,SKELETONS,DERIVATIVES,(-)-FRONDOSIN-B,(+/-)-FRONDOSIN-B,INHIBITOR,FRONDOSIN-B,ENANTIOSELECTIVE TOTAL-SYNTHESIS,cycloheptanes,cycloaddition reactions,furans,natural products,total synthesis},
  language     = {eng},
  number       = {1},
  pages        = {253--262},
  title        = {Total synthesis of (+/−)-frondosin B and (+/−)-5-epi-liphagal by using a concise (4+3) cycloaddition approach},
  url          = {http://dx.doi.org/10.1002/chem.201303273},
  volume       = {20},
  year         = {2014},
}

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