Catalytic asymmetric synthesis of halenaquinone and halenaquinol

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 4876-4877

  Kojima, Akihiko ^a   Takemoto, Toshiyasu ^a   Sodeoka, Mikiko ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; HALENAQUINOL; HALENAQUINONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030017045     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960773z     Document Type: Article

References (26)

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10. Purchased from Aldrich Chemical Co., Inc.
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14. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
15. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
16. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
17. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
18. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
19. Shibasaki, M.; Sodeoka, M. J. Synth. Org. Chem. Jpn. 1994, 52, 956. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem. 1993, 58, 6969. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics 1993, 12, 4188. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett. 1992, 33, 6845. Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1089. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett 1994, 291. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett. 1995, 36, 2051.
20. Compounds 11-13 were prepared as follows ((I) Cochrane, J. S.; Hanson, J. R. J. Chem. Soc., Perkin Trans. 1 1972, 3, 361. (II) Kruithof, K. J. H.; Schmits, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073). (Matrix Presented)
21. Compounds 11-13 were prepared as follows ((I) Cochrane, J. S.; Hanson, J. R. J. Chem. Soc., Perkin Trans. 1 1972, 3, 361. (II) Kruithof, K. J. H.; Schmits, R. F.; Klumpp, G. W. Tetrahedron 1983, 39, 3073). (Matrix Presented)
22. For the use of (Z)-trisubstituted olefins, see: Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1993, 115, 8477.
23. Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
24. The byproducts are iii and iv. (Matrix Presented)
25. The related reaction for the synthesis of indole and furan skeletons has been previously reported. See: Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270.
26. Starostin, E. K.; Mazurchik, A. A.; Ignatenko, A. V.; Nikishin, G. I. Synthesis 1992, 917.