Facile Synthesis of an Octahydrobenzocycloheptenone Derivative Utilising Intramolecular Diels-Alder Reaction

Advanced Synthesis and Catalysis

Volumn 341, Issue 2, 1999, Pages 173-178

  Frey, Barbara ^a   Reißig, Hans Ulrich ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Carbocycles; Cycloadditions; Cycloheptanone; Lewis acids; Titanium

Indexed keywords

EID: 0347713512     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (33)

1. Part 4: J. Schnaubelt, B. Frey, H.-U. Reißig, submitted to Helv. Chim. Acta
2. B. Frey, Dissertation, Technische Hochschule Darmstadt 1992
3. C. H. Heathcock, S. L. Graham, M. C. Pirrung, F. Plavac, C. T. White in The Total Synthesis of Natural Products (Ed. J. ApSimon), John Wiley & Sons, New York 1983, Vol. 5, p. 333
4. H.-J. Liu, E. N. C. Browne, Can. J. Chem. 1981, 59, 601, and references cited therein
5. A. G. González, J. M. Aguiar, J. D. Martin, M. Norte, Tetrahedron Lett. 1975, 2499
6. P. A. Wender, R. M. Keenan, H. Y. Lee, J. Am. Chem. Soc. 1987, 109, 4390, and references cited therein
7. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
8. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
9. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
10. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
11. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
12. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
13. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
14. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
15. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
16. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
17. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
18. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
19. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
20. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
21. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
22. a) For reviews about the intramolecular Diels-Alder reaction, see: W. R. Roush in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford 1991, Vol. 5, p. 513; W. R. Roush, Advances in Cycloaddition, JAI Press Inc., 1990, Vol. 2, p. 91; D. Craig, Chem. Soc. Rev. 1987, 16, 187; D. Craig in Stereoselective Synthesis Methods/Organic Chemistry (Houben-Weyl) (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Georg Thieme Verlag, 1995, Vol. E 21c, p. 2872; b) Syntheses of himachalenes via IMDA: E. Wenkert, K. Naemura, Synth. Commun. 1973, 3, 45; W. Oppolzer, R. L. Snowden, Helv. Chim. Acta 1981, 64, 2592; D. A. Evans, D. H. Brown Ripin, J. S. Johnson, E. A. Shaughnessy, Angew. Chem. 1997, 109, 2208; Angew. Chem. Int. Ed. Engl. 1997, 36, 2119; c) Synthesis towards daphnanes and tiglianes via IMDA: Ref. [6]; L. M. Harwood, B. Jackson, G. Jones, K. Prout, R. M. Thomas, F. J. Witt, J. Chem. Soc., Chem. Commun. 1990, 608; L. M. Harwood, T. Ishikawa, H. Phillips, D. Watkin, J. Chem. Soc., Chem. Commun. 1991, 527; P. C. Bulman Page, D. C. Jennens, R. A. Porter, A. N. Baldock, Synlett 1991, 472, and references cited therein; d) Other IMDAs of 1,8,10-undecatrien-3-ones: P. Tuchinda, V. Prapansiri, W. Naengchomnong, V. Reutrakul, Chem. Lett. 1984, 1427; D. A. Smith, K. Sakan, K. N. Houk, Tetrahedron Lett. 1986, 27, 4877; D. A. Smith, K. N. Houk, Tetrahedron Lett. 1991, 32, 1549; P. A. Grieco, S. T. Handy, J. P. Beck, Tetrahedron Lett. 1994, 35, 2663; M. W. Tuckett, W. J. Watkins, R. J. Whitby, Tetrahedron Lett. 1998, 39, 123
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