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Total synthesis of periplanone-B via intramolecular Diels-Alder reaction with furan-diene and allene-dienophile

Tom De Geyter, Serge Cauwberghs and Pierre De Clercq (UGent)
(1994) BULLETIN DES SOCIETES CHIMIQUES BELGES. 103(7-8). p.433-443
Author
Organization
Abstract
A synthetic route towards (+/-)-periplanone-B is described based on (i) an intramolecular Diels-Alder reaction involving a furan-diene and an allene-dienophile, (ii) selective (C-O)-cleavage in the resulting adduct by lithium di-tert-butylbiphenyl radical anion; (iii) a Grob fragmentation leading to the ten-membered ring, as key-steps.
Keywords
SEX-EXCITANT PHEROMONE, AMERICAN COCKROACH, CARBONYL-COMPOUNDS, (-)-PERIPLANONE-B, REAGENTS, PALLADIUM, HALIDES, ROUTE

Citation

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MLA
De Geyter, Tom, et al. “Total Synthesis of Periplanone-B via Intramolecular Diels-Alder Reaction with Furan-Diene and Allene-Dienophile.” BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 103, no. 7–8, 1994, pp. 433–43, doi:10.1002/bscb.19941030717.
APA
De Geyter, T., Cauwberghs, S., & De Clercq, P. (1994). Total synthesis of periplanone-B via intramolecular Diels-Alder reaction with furan-diene and allene-dienophile. BULLETIN DES SOCIETES CHIMIQUES BELGES, 103(7–8), 433–443. https://doi.org/10.1002/bscb.19941030717
Chicago author-date
De Geyter, Tom, Serge Cauwberghs, and Pierre De Clercq. 1994. “Total Synthesis of Periplanone-B via Intramolecular Diels-Alder Reaction with Furan-Diene and Allene-Dienophile.” BULLETIN DES SOCIETES CHIMIQUES BELGES 103 (7–8): 433–43. https://doi.org/10.1002/bscb.19941030717.
Chicago author-date (all authors)
De Geyter, Tom, Serge Cauwberghs, and Pierre De Clercq. 1994. “Total Synthesis of Periplanone-B via Intramolecular Diels-Alder Reaction with Furan-Diene and Allene-Dienophile.” BULLETIN DES SOCIETES CHIMIQUES BELGES 103 (7–8): 433–443. doi:10.1002/bscb.19941030717.
Vancouver
1.
De Geyter T, Cauwberghs S, De Clercq P. Total synthesis of periplanone-B via intramolecular Diels-Alder reaction with furan-diene and allene-dienophile. BULLETIN DES SOCIETES CHIMIQUES BELGES. 1994;103(7–8):433–43.
IEEE
[1]
T. De Geyter, S. Cauwberghs, and P. De Clercq, “Total synthesis of periplanone-B via intramolecular Diels-Alder reaction with furan-diene and allene-dienophile,” BULLETIN DES SOCIETES CHIMIQUES BELGES, vol. 103, no. 7–8, pp. 433–443, 1994.
@article{199992,
  abstract     = {{A synthetic route towards (+/-)-periplanone-B is described based on (i) an intramolecular Diels-Alder reaction involving a furan-diene and an allene-dienophile, (ii) selective (C-O)-cleavage in the resulting adduct by lithium di-tert-butylbiphenyl radical anion; (iii) a Grob fragmentation leading to the ten-membered ring, as key-steps.}},
  author       = {{De Geyter, Tom and Cauwberghs, Serge and De Clercq, Pierre}},
  issn         = {{0037-9646}},
  journal      = {{BULLETIN DES SOCIETES CHIMIQUES BELGES}},
  keywords     = {{SEX-EXCITANT PHEROMONE,AMERICAN COCKROACH,CARBONYL-COMPOUNDS,(-)-PERIPLANONE-B,REAGENTS,PALLADIUM,HALIDES,ROUTE}},
  language     = {{eng}},
  number       = {{7-8}},
  pages        = {{433--443}},
  title        = {{Total synthesis of periplanone-B via intramolecular Diels-Alder reaction with furan-diene and allene-dienophile}},
  url          = {{http://doi.org/10.1002/bscb.19941030717}},
  volume       = {{103}},
  year         = {{1994}},
}
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