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Volumn , Issue 15, 2008, Pages 2551-2563

Stereoselective synthesis of a cis-1,2-dialkylcyclopentane building block and its application in isoprostane synthesis (5-ent-F2c-IsoP)

Author keywords

Natural products; Protecting groups; Stereoselective synthesis; Total synthesis; Wittig reaction

Indexed keywords


EID: 53549092633     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800010     Document Type: Article
Times cited : (9)

References (75)
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    • We used the following nomenclature system for isoprostanes: D. F. Taber, J. D. Morrow, L. J. Roberts II, Prostaglandins 1997, 53, 63-67
    • We used the following nomenclature system for isoprostanes: D. F. Taber, J. D. Morrow, L. J. Roberts II, Prostaglandins 1997, 53, 63-67.
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    • For the synthesis of IsoPs with 5-exo-radical cyclization as the key step, see, for example: a B. Rondot, T. Durand, J. P. Girard, J. C. Rossi, L. Schio, S. P. Khanapure, J. Rokach, Tetrahedron Lett. 1993, 34, 8245-8248;
    • For the synthesis of IsoPs with 5-exo-radical cyclization as the key step, see, for example: a) B. Rondot, T. Durand, J. P. Girard, J. C. Rossi, L. Schio, S. P. Khanapure, J. Rokach, Tetrahedron Lett. 1993, 34, 8245-8248;
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    • For the synthesis of IsoPs with rhodium-mediated intramolecular cyclopropanation as the key step, see, for example: a) D. F. Taber, K. Kanai, R. Pina, J. Am. Chem. Soc. 1999, 121, 7773-7777;
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    • For the synthesis of IsoPs with palladium-mediated three-component coupling as the key step, see, for example: a) R. C. Larock, N. H. Lee, J. Am. Chem. Soc. 1991, 113, 7815-7816;
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    • II-catalyzed allylic oxidation as the key step, see, for example: a G. Zanoni, A. Porta, A. Meriggi, M. Franzini, G. Vidari, J. Org. Chem. 2002, 67, 6064-6069;
    • II-catalyzed allylic oxidation as the key step, see, for example: a) G. Zanoni, A. Porta, A. Meriggi, M. Franzini, G. Vidari, J. Org. Chem. 2002, 67, 6064-6069;
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    • For the synthesis of IsoPs with a two-component coupling combined with a diastereoselective protonation as the key step, see: A. R. Rodriguez, B. W. Spur, Tetrahedron Lett. 2002, 43, 4575-4579
    • For the synthesis of IsoPs with a two-component coupling combined with a diastereoselective protonation as the key step, see: A. R. Rodriguez, B. W. Spur, Tetrahedron Lett. 2002, 43, 4575-4579.
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    • For the synthesis of IsoPs with ring-opening metathesis as the key step, see: a
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    • R[(-) enantiomer] = 36.4 min (see also Supporting Information).
    • R[(-) enantiomer] = 36.4 min (see also Supporting Information).
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    • Diploma Thesis, University of Heidelberg, chapter 3.5
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    • It should be noted that the reduction of the methyl ester derivative of enone 12 with Noyori's BINAL-H reagent gave acceptable results 55% yield, dr, 8:1, Unfortunately, the methyl ester derivative was not usable in the following synthetic steps
    • It should be noted that the reduction of the methyl ester derivative of enone 12 with Noyori's BINAL-H reagent gave acceptable results (55% yield, dr = 8:1). Unfortunately, the methyl ester derivative was not usable in the following synthetic steps.


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