Nonaflates from 8-oxabicyclo[3.2.1]oct-6-en-3-ones as building blocks for diversity-orientated synthesis: Preparation, Heck-couplings and subsequent Diels- Alder reactions

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1868-1879

  Högermeier, Jens ^a   Reissig, Hans Ulrich ^a   Brüdgam, Irene ^a   Hartl, Hans ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

8 oxabicyclo 3.2.1 oct 6 en 3 one; Alkenyl nonaflates; Diels Alder reaction; Heck coupling; Palladium catalysis

Indexed keywords

2,4 DIMETHYL 8 OXABICYCLO[3.2.1]OCTA 2,6 DIEN 3 YLNONAFLATE; 8 OXABICYCLO[3.2.1]OCTA 2,6 DIEN 3 YLNONAFLATE; ACRYLIC ACID METHYL ESTER; ALKENE DERIVATIVE; FLUORIDE; FURAN DERIVATIVE; KETONE DERIVATIVE; OXYGEN; POLYCYCLIC HYDROCARBON; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; FRAGMENTATION REACTION; HECK REACTION; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 12344278956     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404194     Document Type: Article

References (57)

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3. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
4. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
5. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
6. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
7. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
8. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
9. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
10. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
11. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
12. Selected examples for the use of 8-oxybicyclo[3.2.1]oct-6-en-3-ones in natural product synthesis: a) P. Wolbers, H. M. R. Hoffmann, Synthesis 1999, 797-802; b) P. Wolbers, H. M. R. Hoffmann, Tetrahedron 1999, 55, 1905-1914; c) R. Dunkel, M. Mentzel, H. M. R. Hoffmann, Tetrahedron 1997, 53, 14929-14936; d) R. Dunkel, H. M. R. Hoffmann, Tetrahedron 1999, 55, 8385-8396; e) H. Kim, H. M. R. Hoffmann, Eur. J. Org. Chem. 2000, 2195-2201; f) H. M. R. Hoffmann, R. Dunkel, M. Mentzel, H. Reuter, C. B. W. Stark, Chem. Eur. J. 2001, 7, 4771-4789; g) H. Kim, C. Ziani-Cherif, J. Oh, J. K. Cha, J. Org. Chem. 1995, 60, 792-793; h) M. Lautens, J. T. Colucci, S. Hiebert, N. D. Smith, G. Bouchain, Org. Lett. 2002, 4, 1879-1882; i) M. Lautens, T. A. Stammers, Synlett 2002, 1993-2012; j) M. Lautens, T. A. Stammers, Tetrahedron Lett. 1999, 40, 8317-8321.
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19. For examples of oxabicyclo[3.2.1]octanes as tropane analogues, see: a) P. C. Meltzer, P. Blundell, Y. F. Yong, Z. Chen, C. George, M. D. Gonzales, B. K. Madras, J. Med. Chem. 2000, 45, 2982-2991; b) A. P. Kozikowski, D. Simoni, M. Roberti, R. Rondanin, W. Wang, P. Du, K. M. Johnson, Bioorg. Med. Chem. Lett. 1999, 9, 1831-1836; c) F. Eiden, A. Kainz, R. Gebhard, Arch. Pharm. 1992, 325, 77-82.
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