A general approach toward bakkanes: Short synthesis of (±)- bakkenolide-A (Fukinanolide)

Organic Letters

Volumn 6, Issue 19, 2004, Pages 3345-3347

  Reddy, D Srinivasa ^a,b  

^a Malott Hall ^*  (United States)

^b DR REDDY'S LABORATORIES LTD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BAKKENOLIDE A; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; CYTOTOXICITY; DIELS ALDER REACTION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STEREOCHEMISTRY;

4-BUTYROLACTONE; CATALYSIS; MOLECULAR STRUCTURE; PETASITES; SESQUITERPENES; STEREOISOMERISM;

EID: 4644354263     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048726d     Document Type: Article

References (43)

1. (a) Fischer, N. H.; Oliver, E. J.; Fischer, H. D. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Eds.; Springer-Verlag: New York, 1979; Vol.38, Chapter 2.
2. (b) Silva, L. F., Jr. Synthesis 2001, 671-689.
3. (a) Jamieson, G. R.; Reid, E. H.; Turner, B. P.; Jamieson, A. T. Phytochemistry 1976, 15, 1713-1715.
4. (b) Wu, T.-S.; Kao, M.-S.; Wu, P.-L.; Lin, F.-W.; Shi, L.-S.; Liou, M.-J.; Li, C.-Y. Chem. Pharm. Bull. 1999, 47, 375-382.
5. (a) Nawrot, J.; Harmatha, J.; Novotny, L. Biochem. Syst. Ecol. 1984, 12, 99-101.
6. (b) Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L. Z. Angew. Entomol. 1984, 98, 394-398.
7. (c) Nawrot, J.; Bloszyk, E.; Harmatha, J.; Novotny, L.; Drozdz, B. Acta Entomol. Bohemoslov. 1986, 83, 327-335.
8. (d) Kreckova, J.; Krecek, J.; Harmatha, J. Pr. Nauk. Inst. Chem. Org. Fiz. Politech. Wroclaw. 1988, 33, 105-107.
9. Wu, T.-S.; Kao, M.-S.; Wu, P.-L.; Lin, F.-W.; Shi, L.-S.; Teng, C.-M. Phytochemistry 1999, 52, 901-905.
10. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
11. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
12. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
13. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
14. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
15. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
16. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
17. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
18. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
19. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
20. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
21. For the syntheses of bakkanes and related compounds: (a) Evans, D. A.; Sims, C. L. Tetrahedron Lett. 1973, 14, 4691-4694. (b) Greene, A. E.; Coelho, F.; Depres, J. P.; Brocksom, T. J. Tetrahedron Lett. 1988, 29, 5661-5662. (c) Hamelin, O.; Depres, J.-P.; Greene, A. E.; Tinant, B.; Declercq, J.-P. J. Am. Chem. Soc. 1996, 118, 9992-9993. (d) Hamelin, O.; Wang, Y.; Depres, J.-P.; Greene, A. E. Angew. Chem., Int. Ed. 2000, 39, 4314-4316. (e) Brocksom, T. J.; Coelho, F.; Depres, J.-P.; Greene, A. E.; Freire de Lima, M. E.; Hamelin, O.; Hartmann, B.; Kanazawa, A. M.; Wang, Y. J. Am. Chem. Soc. 2002, 124, 15313-15325 and references cited therein. (f) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S. Tetrahedron Lett. 1994, 35, 429-432. (g) Srikrishna, A.; Nagaraju, S.; Venkateswarlu, S.; Hiremath, U. S.; Reddy, T. J.; Venugopalan, P. J. Chem. Soc., Perkin Trans. 1 1999, 2069-2076. (h) Srikrishna, A.; Reddy, T. J. Arkivoc 2001, Part viii, 9-19 and references cited therein. (i) Back, T. G.; Payne, J. E. Org. Lett. 1999, 1, 663-665. (j) Back, T. G.; Nava-Salgado, V. O.; Payne, J. E. J. Org. Chem. 2001, 66, 4361-4368. (k) Mori, K.; Matsushima, Y. Synthesis 1995, 845. (l) Hayashi, K.; Nakamura, H.; Mitsuhashi, H. Chem. Pharm. Bull. 1973, 21, 2806-2807.
22. (a) Abe, N.; Onoda, R.; Shirahata, K.; Kato, T.; Woods, M. C.; Kitahara, Y. Tetrahedron Lett. 1968, 9, 369-373.
23. (b) Naya, K.; Takagi, I.; Hayashi, M.; Nakamura, S.; Kobayashi, M.; Katsumura, S. Chem. Ind. (London) 1968, 318-320.
24. Previously this compound was prepared in minimum of 3 steps. (a) Tsuji J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 19, 2075-2078. (b) Gaoni, Y. J. Org. Chem, 1981, 46, 4502-4510. (c) Yamada, S.; Suzuki, H.; Naito, H.; Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1987, 332-333.
25. Previously this compound was prepared in minimum of 3 steps. (a) Tsuji J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 19, 2075-2078. (b) Gaoni, Y. J. Org. Chem, 1981, 46, 4502-4510. (c) Yamada, S.; Suzuki, H.; Naito, H.; Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1987, 332-333.
26. Previously this compound was prepared in minimum of 3 steps. (a) Tsuji J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 19, 2075-2078. (b) Gaoni, Y. J. Org. Chem, 1981, 46, 4502-4510. (c) Yamada, S.; Suzuki, H.; Naito, H.; Nomoto, T.; Takayama, H. J. Chem. Soc., Chem. Commun. 1987, 332-333.
27. (a) Bal, S. A.; Helquist, P. Tetrahedron Lett. 1981, 22, 3933-3936.
28. (b) Mulholland, R. L.; Chamberlin, A. R. J. Org. Chem. 1988, 53, 1082-1085.
29. (c) Bull, J. R.; Gordon, R.; Hunter, R. J. Chem. Soc., Perkin Trans. 1 2000, 3129-3139.
30. Stereochemistry was assigned on the basis of literature precedence; see: refs 10, 11, and 13.
31. For the synthesis of eremophilanes using similar Diels-Alder reaction, see: Reddy, D. S.; Kozmin, S. A. J. Org. Chem. 2004, 69, 4860-4862.
32. For other related Diels-Alder reactions: (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc. 1989, 111, 6070-6081. (b) Hashimoto, Y.; Nagashima, T.; Kobayashi, K.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 6349-6358. (c) Winkler, J. D.; Kim, H. S.; Kim, S.; Penkett, C. S.; Bhattacharya, S. K.; Ando, K.; Houk, K. N. J. Org. Chem. 1997, 62, 2957-2962. (d) Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 3471-3478. (e) Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
33. For other related Diels-Alder reactions: (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc. 1989, 111, 6070-6081. (b) Hashimoto, Y.; Nagashima, T.; Kobayashi, K.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 6349-6358. (c) Winkler, J. D.; Kim, H. S.; Kim, S.; Penkett, C. S.; Bhattacharya, S. K.; Ando, K.; Houk, K. N. J. Org. Chem. 1997, 62, 2957-2962. (d) Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 3471-3478. (e) Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
34. For other related Diels-Alder reactions: (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc. 1989, 111, 6070-6081. (b) Hashimoto, Y.; Nagashima, T.; Kobayashi, K.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 6349-6358. (c) Winkler, J. D.; Kim, H. S.; Kim, S.; Penkett, C. S.; Bhattacharya, S. K.; Ando, K.; Houk, K. N. J. Org. Chem. 1997, 62, 2957-2962. (d) Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 3471-3478. (e) Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
35. For other related Diels-Alder reactions: (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc. 1989, 111, 6070-6081. (b) Hashimoto, Y.; Nagashima, T.; Kobayashi, K.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 6349-6358. (c) Winkler, J. D.; Kim, H. S.; Kim, S.; Penkett, C. S.; Bhattacharya, S. K.; Ando, K.; Houk, K. N. J. Org. Chem. 1997, 62, 2957-2962. (d) Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 3471-3478. (e) Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
36. For other related Diels-Alder reactions: (a) Bonnesen, P. V.; Puckett, C. L.; Honeychuck, R. V.; Hersh, W. H. J. Am. Chem. Soc. 1989, 111, 6070-6081. (b) Hashimoto, Y.; Nagashima, T.; Kobayashi, K.; Hasegawa, M.; Saigo, K. Tetrahedron 1993, 49, 6349-6358. (c) Winkler, J. D.; Kim, H. S.; Kim, S.; Penkett, C. S.; Bhattacharya, S. K.; Ando, K.; Houk, K. N. J. Org. Chem. 1997, 62, 2957-2962. (d) Baillie, L. C.; Batsanov, A.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 3471-3478. (e) Ge, M.; Stoltz, B. M.; Corey, E. J. Org. Lett. 2000, 2, 1927-1929.
37. Compound 6 could not be isolated in pure form, and the crude reaction mixture was subjected to the next step as such.
38. (a) Sauer, J. Angew. Chem., Int. Ed. Engl. 1967, 6, 16.
39. (b) Houk, K. N.; Strozier, R. W. J. Am. Chem, Soc. 1973, 95, 4094-4096
40. (c) Houk, K. N. Acc. Chem, Res. 1975, 8, 361.
41. (d) Eisenstein, O.; LeFour, J. M.; Anh, N. T., Hudson, R. F. Tetrahedron 1977, 33, 523.
42. Mander, L. N.; Sethi. S. P. Tetrahedron Lett. 1983, 24, 5425-5428.
43. Miller, R. D.; McKean, D. R. Synthesis 1979, 730-732.