Enantioselective total synthesis of the marine alkaloid Lepadin B

Journal of Organic Chemistry

Volumn 64, Issue 7, 1999, Pages 2182-2183

  Toyooka, Naoki ^a   Okumura, Maiko ^a   Takahata, Hiroki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTINEOPLASTIC ALKALOID; LEPADIN B; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CYCLIZATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; MARINE ENVIRONMENT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033515505     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990141n     Document Type: Article

References (36)

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2. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1993; Vol. 43, pp 185-288. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1998; Vol. 50, pp 141-169.
3. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
4. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
5. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
6. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
7. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
8. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
9. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
10. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
11. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
12. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
13. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
14. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
15. Several strategies for the chiral synthesis of the cis-decahydroquinoline alkaloid pumiliotoxin C have been reported; see: Oppolzer, W.; Flaskamp, E. Helv. Chim. Acta 1977, 60, 204-207. Royer, M. B. J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569-1572. Schultz, A. G.; McCloskey, P. J.; Court, J. J. J. Am. Chem. Soc. 1987, 109, 6493-6502. Murahashi, S.; Sasao, S.; Saito, E.; Naota, E. J. Org. Chem. 1992, 57, 2521-2523; Tetrahedron 1993, 49, 8805-8826. Comins, D. L.; Dehghani, A. J. Chem. Soc., Chem. Commun. 1993, 1838-1839. Naruse, M.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1994, 35, 9213-9216; J. Chem. Soc., Perkin Trans. 1 1996, 1113-1124. Toyota, M.; Asoh, T.; Fukumoto, K. Tetrahedron Lett. 1996, 37, 4401-4404. Davies, S. G.; Bhalay, G. Tetrahedron: Asymmetry 1996, 7, 1595-1596. Riechers, T.; Krebs, H. C.; Wartchow, R.; Habermehl, G. Eur. J. Org. Chem. 1998, 2641-2646. Two strategies for the construction of trans-decahydroquinoline ring system have been reported; see: McCloskey, P. J.; Schultz, A. G. J. Org. Chem. 1988, 53, 1380-1383. Comins, D. L.; Dehghani, A. J. Org. Chem. 1995, 60, 794-795.
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20. Satisfactory analytical and spectral data were obtained for all new compounds.
21. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
22. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
23. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
24. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
25. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
26. Recently, this type of vinyltriflate has been used as a tool for the synthesis of several types of compound; see: Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737-3744. Foti, C. J.; Comins, D. L. J. Org. Chem. 1995, 60, 2656-2657. Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257-8260; J. Org. Chem. 1997, 62, 3592-3596. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550-4551. Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K J. Org. Chem. 1998, 63, 3810-3811.
27. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
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29. The stereochemistry of the newly formed C-2 and C-3 positions in 9 was anticipated to be 2S, 3R according to our previous investigation on the Michael addition reaction of the similar system; see: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943-945. Toyooka, N. Tanaka, K. Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553-9574.
30. The stereochemistry of the newly formed C-2 and C-3 positions in 9 was anticipated to be 2S, 3R according to our previous investigation on the Michael addition reaction of the similar system; see: Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943-945. Toyooka, N. Tanaka, K. Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553-9574.
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33. Highly stereoselective 1,4-addition of this type of enone has been reported; 3ee:. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. Ibuka, T.; Masaki, N.; Saji, I.; Tanaka, K.; Inubushi, Y. Chem. Pharm. Bull. 1975, 23, 2779-2790.
34. Highly stereoselective 1,4-addition of this type of enone has been reported; 3ee:. Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103-4110. Ibuka, T.; Masaki, N.; Saji, I.; Tanaka, K.; Inubushi, Y. Chem. Pharm. Bull. 1975, 23, 2779-2790.
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