Synthesis 2010(13): 2308-2312  
DOI: 10.1055/s-0029-1218793
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

[2+2]-Photocycloaddition Reactions of Tetronic Acid Esters and Amides

Jörg P. Hehn, Diego Gamba-Sánchez, Michael Kemmler, Martin Fleck, Birte Basler, Thorsten Bach*
Lehrstuhl für Organische Chemie I, Technische Universität München, Lichtenbergstr. 4, 85747 Garching, Germany
Fax: +49(89)28913315; e-Mail: [email protected];
Further Information

Publication History

Received 15 April 2010
Publication Date:
20 May 2010 (online)

Abstract

Tetronic acid esters and amides, which are readily available from the corresponding tetronic acids, serve as useful starting materials in an intra- or intermolecular [2+2]-photocycloaddition reaction. Typical reaction conditions are irradiation at λ = 254 nm in diethyl ether or an alcohol as the solvent. The bi-, tri- or tetracyclic products so obtained can be further utilized by ring opening either of the lactone or the cyclobutane ring. Lactone ring opening led to the use of a tetramide photocycloaddition product as a conformationally restricted β-proline analogue and to an application of a tetronate photocycloaddition product in the total synthesis of punctaporonin C.

    References

  • 4a Hehn JP. Müller C. Bach T. In Handbook of Synthetic Photochemistry   Albini A. Fagnoni M. Wiley-VCH; Weinheim: 2010.  p.171 
  • 4b Hoffmann N. Chem. Rev.  2008,  108:  1052 
  • 4c Iriondo-Alberdi J. Greaney MF. Eur. J. Org. Chem.  2007,  4801 
  • 4d Fleming SA. In Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry)   Vol. 12:  Griesbeck AG. Mattay J. Dekker; New York: 2005.  p.141 
  • 4e Margaretha P. In Synthetic Organic Photochemistry (Molecular and Supramolecular Photochemistry)   Vol. 12:  Griesbeck AG. Mattay J. Dekker; New York: 2005.  p.211 
  • 4f Pete JP. In CRC Handbook of Organic Photochemistry and Photobiology   2nd ed.:  Horspool WM. Lenci F. CRC Press; Boca Raton: 2004.  p.71-1  
  • 4g Bach T. Synthesis  1998,  683 
  • 4h Fleming SA. Bradford CL. Gao JJ. In Organic Photochemistry (Molecular and Supramolecular Photochemistry)   Vol. 1:  Ramamurthy V. Schanze KS. Dekker; New York: 1997.  p.187 
  • 4i Pete J.-P. In Advances in Photochemistry   Vol. 21:  Neckers DC. Volman DH. v.  Bünau G. Wiley; New York: 1996.  p.135 
  • 4j Mattay J. Conrads R. Hoffmann R. In Methoden der Organischen Chemie (Houben-Weyl)   4th ed., Vol. E 21c:  Helmchen G. Hoffmann RW. Mulzer J. Schaumann E. Thieme; Stuttgart: 1995.  p.3085 
  • 4k Crimmins MT. Reinhold TL. Org. React.  1993,  44:  297 
  • 4l Crimmins MT. Chem. Rev.  1988,  88:  1453 
  • 4m Baldwin SW. Org. Photochem.  1981,  5:  123 
  • 4n Bauslaugh PG. Synthesis  1970,  287 
  • 5a Kemmler M. Bach T. Angew. Chem. Int. Ed.  2003,  42:  4824 ; Angew. Chem. 2003, 115, 4973
  • 5b Kemmler M. Herdtweck E. Bach T. Eur. J. Org. Chem.  2004,  4582 
  • 6 Fleck M. Bach T. Angew. Chem. Int. Ed.  2008,  47:  6189 ; Angew. Chem. 2008, 120, 6284
  • 7a Seebach D. Matthews JL. J. Chem. Soc., Chem. Commun.  1997,  2015 
  • 7b Cheng RP. Gellman SH. DeGrado WF. Chem. Rev.  2001,  101:  3219 
  • 8 Basler B. Schuster O. Bach T. J. Org. Chem.  2005,  70:  9798 
  • 9 Curtius FW. Scharf H.-D. Tetrahedron: Asymmetry  1996,  7:  2957 
  • 10a Schuster DI. In CRC Handbook of Organic Photochemistry and Photobiology   2nd ed.:  Horspool WM. Lenci F. CRC Press; Boca Raton: 2004.  p.72-1  
  • 10b Schuster DI. Lem GN. Kaprinidis A. Chem. Rev.  1993,  93: 
  • 11a Srinivasan R. Hill Carlough K. J. Am. Chem. Soc.  1967,  89:  4932 
  • 11b Liu RSH. Hammond GS. J. Am. Chem. Soc.  1967,  89:  4936 
  • 12 Vogt F. Jödicke K. Schröder J. Bach T. Synthesis  2009,  4268 
  • 13 Hehn JP. Kemmler M. Bach T. Synlett  2009,  1281 
  • 14 Fleck M. Yang C. Wada T. Inoue Y. Bach T. Chem. Commun.  2007,  822 
  • 15a Anderson JR. Edwards RL. Poyser JP. Whalley AJS. J. Chem. Soc., Perkin Trans. 1  1988,  823 
  • 15b Anderson JR. Edwards RL. Freer AA. Mabelis RP. Poyser JP. Spencer H. Whalley AJS. J. Chem. Soc., Chem. Commun.  1984,  917 
  • 15c Anderson JR. Briant CE. Edwards RL. Mabelis RP. Poyser JP. Spencer H. Whalley AJS. Freer AA. J. Chem. Soc., Chem. Commun.  1986,  984 
  • 16a Sato T. Yoshimatsu K. Otera J. Synlett  1995,  843 
  • 16b Bajwa JS. Anderson RC. Tetrahedron Lett.  1990,  31:  6973 
  • 16c Farina F. Martín MV. Sánchez F. Maestro MC. Martín MR. Synthesis  1983,  397 
  • 16d Martín MR. Mateo AI. Tetrahedron: Asymmetry  1994,  5:  1385 
  • 16e Chen Q. Geng Z. Huang B. Tetrahedron: Asymmetry  1995,  6:  401 
1

Present address: BioFocus DPI AG, Gewerbestrasse 16, 4123 Allschwil, Switzerland.

2

Present address: Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Straße 65, 88397 Biberach/Riß, Germany.

3

Present address: Maiwald Patentanwalts-GmbH, Elisenstraße 3, 80335 München, Germany.