Facile Synthesis of Enantiomerically Pure Architectures Based on Triphenylene Ketals

Abstract

Employing naturally derived (-)-isosteviol for the construction of chirally modified triphenylene ketals resulted in very rigid supramolecular clefts that exhibit a mutual distance of about 20 Å between the functional groups. Since the stereodirecting groups of these novel architectures are located in the backbone, an open receptor geometry is established.

Key words

receptor - supramolecular chemistry - terpenoids - chirality - triphenylene ketal

References

• 1a Moberg C. Angew. Chem. Int. Ed.  2006,  45:  2929 
• 1b Moberg C. Angew. Chem. Int. Ed.  1998,  37:  248 
• 1c Rebek J. Angew. Chem., Int. Ed. Engl.  1990,  29:  245 
• 2 Waldvogel SR. Fröhlich R. Schalley CA. Angew. Chem. Int. Ed.  2000,  39:  2472 
• 3 Schopohl MC. Siering C. Kataeva O. Waldvogel SR. Angew. Chem. Int. Ed.  2003,  42:  2620 
• 4 Siering C. Grimme S. Waldvogel SR. Chem. Eur. J.  2005,  11:  1877 
• 5 Schophol MC. Faust A. Mirk D. Fröhlich R. Kataeva O. Waldvogel SR. Eur. J. Org. Chem.  2005,  2987 
• 6 Schophol MC. Bergander K. Kataeva O. Fröhlich R. Waldvogel SR. Synthesis  2003,  2689 
• 7a Bartlett PD. Knox LH. Org. Synth. Coll. Vol. V   John Wiley & Sons; London: 1973.  p.689 
• 7b Fabris F. Zambrini L. Rosso E. De Lucchi O. Eur. J. Org. Chem.  2004,  3313 
• 8 Schophol MC. PhD Thesis   University of Münster; Germany: 2005. 
• 9a Mosettig E. Nes WR. J. Org. Chem.  1955,  20:  884 
• 9b Mosettig E. Beglinger U. Dolder F. Lichti H. Quitt P. Waters JA. J. Am. Chem. Soc.  1963,  85:  2305 
• 10 Starraat AN. Kirby CW. Pocs R. Brandle JE. Phytochemistry  2002,  59:  367 
• 11 Alfonsov VA. Bakaleynik GA. Gubaidullin AT. Kataev VE. Kovylijaeva GI. Konovalov AI. Litvinov IA. Strobykina IY. Andreeva OV. Korochina MG. Mendeleev Commun.  1999,  227 
• 12 Coates MC. J. Org. Chem.  1987,  52:  2065 
• 13a Waldvogel SR. Mirk D. Tetrahedron Lett.  2000,  41:  4769 
• 13b Waldvogel SR. Mirk D. Herbrüggen J. GDCh Monographien  2001,  23:  33 
• 14 Waldvogel SR. Wartini AR. Rasmussen PH. Rebek J. Tetrahedron Lett.  1999,  40:  3515 
• 15a Kramer B. Fröhlich R. Waldvogel SR. Eur. J. Org. Chem.  2003,  3549 
• 15b Kramer B. Waldvogel SR. Angew. Chem. Int. Ed.  2004,  43:  2446 
• 16 Müller U. Angew. Chem., Int. Ed. Engl.  1981,  20:  692 
• 17 Gassmann PG. Schenck WN. J. Org. Chem.  1977,  42:  918 
• 18 Wolff O. Waldvogel SR. Synthesis  2004,  1303 
• 19 Ninomiya K. Shioiri T. Yamada S. Tetrahedron  1974,  30:  2151 
• 20 Breitmaier E. Terpenes: Flavors, Fragrances, Pharmaca, Pheromones   Wiley-VCH; Weinheim: 2006. 
• Programs used, data collection:
• 21a

  COLLECT, Nonius, B.V., 1998. Data reduction, Denzo-SMN, see:

• 21b Otwinowski Z. Minor W. Methods Enzymol.  1997,  276:  307 
• Absorption correction, Denzo, see:
• 21c Otwinowski Z. Borek D. Majewski W. Minor W. Acta Crystallogr., Sect. A  2003,  59:  228 
• Structure solution SIR97:
• 21d Altomare A. Burla MC. Camalli M. Cascarano GL. Giacovazzo C. Guagliardi A. Moliterni AGG. Polidori G. Spagna R. J. Appl. Crystallogr.  1999,  32:  115 
• Implemented in the WINGX package:
• 21e Farrugia LJ. J. Appl. Crystallogr.  1999,  32:  837 
• Structure refinement by full-matrix least-squares against F² using SHELXL-97:
• 21f

  Sheldrick, G. M. Universität Göttingen, 1997.

• 21g

  The absolute configuration was assessed by Flack’s enantiopole parameter 0.02(6).

22

CCDC 630916 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone], E-mail: [e-mail]].