Total synthesis of methyl picrotoxate via the palladium catalyzed enyne cycloisomerization reaction

Tetrahedron

Volumn 54, Issue 15, 1998, Pages 3693-3704

  Krische, Michael J ^a   Trost, Barry M ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHYLPICROTOXATE; PALLADIUM; PICROTOXININ; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; ISOMERISM; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 0032499171     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00103-3     Document Type: Article

References (23)

1. 1. Trost, B.M.; Krische, M.J. J. Am. Chem. Soc. 1996, 118, 233.
2. 2. Trost, B.M.; Tasker, A.S.; Ruther, G.; Brandes, A. J. Am. Chem. Soc. 1991, 113, 670.
3. 3. Conroy, H. J. Am. Chem. Soc. 1957, 79, 5550.
4. 4. Sharma, N; Rambabu, M.; Sranjaneyulu, A. Indian J. Chem. 1987, 26b, 189.
5. 5. Schroder, M. Chem. Rev. 1980, 80, 187.
6. 6. Horrmann, P. Ber. 1913, 46, 2793. For β-bromopicrotoxinic acid see: Meyer, R.J.; Bruger, P. Ber. 1898, 31, 2958.
7. 6. Horrmann, P. Ber. 1913, 46, 2793. For β-bromopicrotoxinic acid see: Meyer, R.J.; Bruger, P. Ber. 1898, 31, 2958.
8. 7. Krische, M.J.; Trost, B.M. manuscript in preparation.
9. 8. House, H.O.; Ro, R.S. J. Am. Chem. Soc. 1957, 80, 182.
10. 9. Sharpless, K.B. J. Chem. Soc. Chem. Commun. 1970, 1450. Horrmann, P. Ber. 1913, 46, 2793.
11. 9. Sharpless, K.B. J. Chem. Soc. Chem. Commun. 1970, 1450. Horrmann, P. Ber. 1913, 46, 2793.
12. 10. Horrmann, P. Ber. 1913, 46, 2793.
13. 11. Mori, K.; Tominaga, M.; Takigawa, T.; Matsui, M. Synthesis 1973, 790.
14. 12. Hormann, P. Ann. 1916, 411, 273.
15. 13. X-Ray crystallographic analysis performed by Professor Dan Stack.
16. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
17. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
18. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
19. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
20. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
21. 14. Picrodendrins C and D: Ohmoto, T.; Koike, K.; Fukuda, H.; Mitsunaga, K.; Ogata, K.; Kagei, K. Chem. Pharm. Bull. 1989, 37, 2988. Picrodendrins E, F, and I: Koike, K. Ohmoto, T.; Kawai, T.; Sato, T. Phytochemistry 1991, 30, 3353. Picrodendrins B,G, and J: Koike, K.; Fukuda, H.; Mitsunaga, K.; Ohmoto, T. Chem. Pharm. Bull. 1991, 39, 934. Picrodendrins K-R: Suzuki, Y.; Koike, K.; Ohmoto, T. Phytochemistry 1992, 31, 2059. Picrodendrins S and T: Koike, K.; Suzuki, Y.; Ohmoto, T. Phytochemistry 1994, 35, 701. Picrodendrins U, V and W: Nagahisa, M.; Koike, K.; Narita, M.; Ohmoto, T. Tetrahedron 1994, 50, 10859.
22. 15. Ozoe, Y.; Hasagawa, H.; Mochida, K.; Koike, K.; Suzuki, Y.; Nagahisa, M.; Ohmoto, T. Biosci. Biotech. Biochem. 1994, 58, 1506.
23. 16. Perrin, D.D.; Armarego, W.L.F. Purification of Laboratory Chemicals, 3rd Ed. Permagon Press: New York, 1988.