Metallated α-alkoxypropargyl and γ-alkoxyallenyl derivatives: Applications in some aldol reactions towards diterpene synthesis

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5519-5522

  Anies, Claude ^a   Lallemand, Jean Yves ^a   Pancrazi, Ange ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; DITERPENE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030605843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01186-0     Document Type: Article

References (44)

1. 1) Waddell, T. G.; Osborne, C. B.; Collison, R.; Levine, M. J.; Cross, M. C.; Silverton, J. V.; Fales, H. M.; Sokoloski, E. A. J. Org. Chem. 1983, 48, 4450-53.
2. 2) Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J.; Fehlhaber, H.-W. Tetrahedron Lett. 1977, 1669-1672. Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J. J. Chem. Soc., Perkin Trans 1 1982, 767-71.
3. 2) Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J.; Fehlhaber, H.-W. Tetrahedron Lett. 1977, 1669-1672. Bhat, S. V.; Bajwa, B. S.; Dornauer, H.; de Souza, N. J. J. Chem. Soc., Perkin Trans 1 1982, 767-71.
4. 3) For the total synthesis of (±)-erigerol see: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta. 1990, 73, 1108-38. For synthetic approaches of erigerol see: Somoza, C.; Colombo, M. I.; Olivieri, A. C.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1987, 17, 1727-33. Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39. Preite, M. D.; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
5. 3) For the total synthesis of (±)-erigerol see: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta. 1990, 73, 1108-38. For synthetic approaches of erigerol see: Somoza, C.; Colombo, M. I.; Olivieri, A. C.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1987, 17, 1727-33. Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39. Preite, M. D.; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
6. 3) For the total synthesis of (±)-erigerol see: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta. 1990, 73, 1108-38. For synthetic approaches of erigerol see: Somoza, C.; Colombo, M. I.; Olivieri, A. C.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1987, 17, 1727-33. Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39. Preite, M. D.; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
7. 3) For the total synthesis of (±)-erigerol see: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta. 1990, 73, 1108-38. For synthetic approaches of erigerol see: Somoza, C.; Colombo, M. I.; Olivieri, A. C.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1987, 17, 1727-33. Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39. Preite, M. D.; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
8. 3) For the total synthesis of (±)-erigerol see: Kienzle, F.; Stadlwieser, J.; Rank, W.; Mergelsberg, I. Tetrahedron Lett. 1988, 29, 6479-82. Kienzle, F.; Stadlwieser, J.; Rank, W.; Schönholzer, P. Helv. Chim. Acta. 1990, 73, 1108-38. For synthetic approaches of erigerol see: Somoza, C.; Colombo, M. I.; Olivieri, A. C.; Gonzalez-Sierra, M.; Ruveda, E. A. Synth. Commun. 1987, 17, 1727-33. Colombo, M. I.; Zinczuk, J.; Bacigaluppo, J. A.; Somoza, C.; Ruveda, E. A. J. Org. Chem. 1990, 55, 5631-39. Preite, M. D.; Ruveda, E. A. Synth. Commun. 1994, 24, 2809-25.
9. 4) Anies, C.; Lallemand, J.-Y.; Pancrazi, A. Tetrahedron Lett., accompanying note.
10. 5) Quintard, J.-P.; Dumartin, G.; Elissondo, B.; Rahm, A.; Pereyre, M. Tetrahedron 1989, 45, 1017-28. Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Org. Chem. 1983, 48, 1559-60. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1989, 1521-27. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-52. See also a review: Poli, G.; Scolastico, C. Chemtracts 1991, 298-306.
11. 5) Quintard, J.-P.; Dumartin, G.; Elissondo, B.; Rahm, A.; Pereyre, M. Tetrahedron 1989, 45, 1017-28. Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Org. Chem. 1983, 48, 1559-60. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1989, 1521-27. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-52. See also a review: Poli, G.; Scolastico, C. Chemtracts 1991, 298-306.
12. 5) Quintard, J.-P.; Dumartin, G.; Elissondo, B.; Rahm, A.; Pereyre, M. Tetrahedron 1989, 45, 1017-28. Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Org. Chem. 1983, 48, 1559-60. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1989, 1521-27. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-52. See also a review: Poli, G.; Scolastico, C. Chemtracts 1991, 298-306.
13. 5) Quintard, J.-P.; Dumartin, G.; Elissondo, B.; Rahm, A.; Pereyre, M. Tetrahedron 1989, 45, 1017-28. Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Org. Chem. 1983, 48, 1559-60. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1989, 1521-27. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-52. See also a review: Poli, G.; Scolastico, C. Chemtracts 1991, 298-306.
14. 5) Quintard, J.-P.; Dumartin, G.; Elissondo, B.; Rahm, A.; Pereyre, M. Tetrahedron 1989, 45, 1017-28. Quintard, J.-P.; Elissondo, B.; Pereyre, M. J. Org. Chem. 1983, 48, 1559-60. Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Perkin Trans 1 1989, 1521-27. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1043-52. See also a review: Poli, G.; Scolastico, C. Chemtracts 1991, 298-306.
15. 6) Degl'Innocenti, A.; Stucchi, E.; Capperucci, A.; Mordini, A.; Reginato, G., Ricci, A. Synlett 1992, 332-34.
16. 7) Merlic, C. A.; Albaneze, J. Tetrahedron Lett. 1995, 36, 1007-10. ibid 1995, 36, 1011-14.
17. 7) Merlic, C. A.; Albaneze, J. Tetrahedron Lett. 1995, 36, 1007-10. ibid 1995, 36, 1011-14.
18. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
19. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
20. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
21. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
22. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
23. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
24. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
25. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
26. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
27. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
28. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
29. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
30. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
31. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
32. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
33. 8) For a recent review on propargyl and allenyl organometallics see: Yamamoto, H. in "Comprehensive Organic Chemistry", Trost B. M. and Fleming, I. Eds, Pergamon, 1991, vol 2, 81-98. Mantione, R.; Leroux, Y. Tetrahedron Lett. 1971, 593-94. Leroux, Y.; Roman, C. Tetrahedron Lett. 1973, 2585-86. Carlson, R. M.; Isidor, J. L. Tetrahedron Lett. 1973, 4819-22. Stähle, M.; Schlosser, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 875-76. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621-24. Yamakado, Y.; Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Am. Chem. Soc. 1981, 103, 5568-70. Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-82. See also: Kruithof, K. J. H.; Schmitz, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073-81. Pappalardo, P.; Ehlinger, E.; Magnus, P. Tetrahedron Lett. 1982, 23, 309-12. Reich, H. J.; Eisenhart, E. K.; Olson, R. E.; Kelly, M. J. J. Am. Chem. Soc. 1986, 108, 7791-800. Whitby, R.; Kocienski, P. J. Chem. Soc., Chem. Commun. 1987, 906-07. Matsuoka, R.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1987, 28, 1299-1302. Takeda, T.; Ohshima, H.; Inoue, M.; Togo, A.; Fujiwara, T. Chem. Lett. 1987, 1345-48. Harada, T.; Osada, A.; Oku, A. Tetrahedron Lett. 1995, 36, 723-24. For a rewiew on alkoxyallenes see: Zimmer, R. Synthesis 1993, 165-78.
34. 9) Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-96. Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. For synthesis of chiral allene derivatives see Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400.
35. 9) Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-96. Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. For synthesis of chiral allene derivatives see Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400.
36. 9) Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-96. Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. For synthesis of chiral allene derivatives see Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400.
37. 9) Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-96. Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. For synthesis of chiral allene derivatives see Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400.
38. 9) Haruta, R.; Ishiguro, M.; Furuta, K.; Mori, A.; Ikeda, N.; Yamamoto, H. Chem. Lett. 1982, 1093-96. Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-27. For synthesis of chiral allene derivatives see Dreller, S.; Dyrbusch, M.; Hoppe, D. Synlett 1991, 397-400.
39. 10) Hiraoka, H.; Furuta, K.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2777-80.
40. 11) Anies, C., Thesis, Ecole Polytechnique, Palaiseau, France, December 1995.
41. 3), 33.7 (C-4), 38.5 (C-2), 42.9 (C-5), 48.4 (C-10), 67.1 (C-7), 69.9 (C-11), 74.9 (C-2′), 75.2 (C-6), 84.0 (C-1), 84.0 (C-1′), 105.3 (C-8), 159.5 (C-9).
42. 13) Brandsma, L. "Preparative acetylenic chemistry", Elsevier, New York, 1988.
43. 3), 94.30 (C-2), 107.26 (C-3).
44. 3), 119.6 (C-1), 163.9 (C-3), 207.4 (C-2).