Asymmetric synthesis of chiral spirocyclanes: A new route to the optically active spiro[cyclopentane-1,1′-indan]-2,5-dione system

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1817-1820

  Kita, Yasuyuki ^a   Kitagaki, Shinji ^a   Imai, Reiko ^a   Okamoto, Sachi ^a   Mihara, Sachiko ^a   Yoshida, Yutaka ^a   Akai, Shuji ^a   Fujioka, Hiromichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTANE DERIVATIVE; INDAN DERIVATIVE; SPIRO COMPOUND; SPIRO[CYCLOPENTANE 1,1' INDAN] 2,5 DIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029937840     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00126-8     Document Type: Article

References (29)

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3. R. C. Pandey, M. W. Toussaint, R. M. Stroshane, C. C. Kalita, A. A. Aszalos, A. L. Garretson, T. T. Wei, K. M. Byrne, R. F. Geoghegan Jr., R. J. White, J. Antibiot. 1981, 34, 1389-1401; R. Misra, R. C. Pandey, J. V. Silverton, J. Am. Chem. Soc. 1982, 104, 4478-4479; R. Misra, R. C. Pandey, B. D. Hilton, P. P. Roller, J. V. Silverton, J. Antibiot. 1987, 40, 786-802.
4. (a) For the total synthesis of racemic fredericamycin A, see: T. R. Kelly, S. H. Bell, N. Ohashi, R. J. Armstrong-Chong, J. Am. Chem. Soc. 1988, 110, 6471-6480; A. V. R. Rao, A. K. Singh, B. V. Rao, K. M. Reddy, Tetrahedron Lett. 1993, 34, 2665-2668; L. Saint-James, C. Lila, J. Z. Xu, L. Moreau, B. Pfeiffer, G. Eck, L. Pelsez, C. Rolando, M. Julia, Bull. Soc. Chim. France 1993, 130, 447-449; J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926; D. L. J. Clive, Y. Tao, A. Khodabocus, Y. -J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, ibid. 1994, 116, 11275-11286.
5. (a) For the total synthesis of racemic fredericamycin A, see: T. R. Kelly, S. H. Bell, N. Ohashi, R. J. Armstrong-Chong, J. Am. Chem. Soc. 1988, 110, 6471-6480; A. V. R. Rao, A. K. Singh, B. V. Rao, K. M. Reddy, Tetrahedron Lett. 1993, 34, 2665-2668; L. Saint-James, C. Lila, J. Z. Xu, L. Moreau, B. Pfeiffer, G. Eck, L. Pelsez, C. Rolando, M. Julia, Bull. Soc. Chim. France 1993, 130, 447-449; J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926; D. L. J. Clive, Y. Tao, A. Khodabocus, Y. -J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, ibid. 1994, 116, 11275-11286.
6. (a) For the total synthesis of racemic fredericamycin A, see: T. R. Kelly, S. H. Bell, N. Ohashi, R. J. Armstrong-Chong, J. Am. Chem. Soc. 1988, 110, 6471-6480; A. V. R. Rao, A. K. Singh, B. V. Rao, K. M. Reddy, Tetrahedron Lett. 1993, 34, 2665-2668; L. Saint-James, C. Lila, J. Z. Xu, L. Moreau, B. Pfeiffer, G. Eck, L. Pelsez, C. Rolando, M. Julia, Bull. Soc. Chim. France 1993, 130, 447-449; J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926; D. L. J. Clive, Y. Tao, A. Khodabocus, Y. -J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, ibid. 1994, 116, 11275-11286.
7. (a) For the total synthesis of racemic fredericamycin A, see: T. R. Kelly, S. H. Bell, N. Ohashi, R. J. Armstrong-Chong, J. Am. Chem. Soc. 1988, 110, 6471-6480; A. V. R. Rao, A. K. Singh, B. V. Rao, K. M. Reddy, Tetrahedron Lett. 1993, 34, 2665-2668; L. Saint-James, C. Lila, J. Z. Xu, L. Moreau, B. Pfeiffer, G. Eck, L. Pelsez, C. Rolando, M. Julia, Bull. Soc. Chim. France 1993, 130, 447-449; J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926; D. L. J. Clive, Y. Tao, A. Khodabocus, Y. -J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, ibid. 1994, 116, 11275-11286.
8. (a) For the total synthesis of racemic fredericamycin A, see: T. R. Kelly, S. H. Bell, N. Ohashi, R. J. Armstrong-Chong, J. Am. Chem. Soc. 1988, 110, 6471-6480; A. V. R. Rao, A. K. Singh, B. V. Rao, K. M. Reddy, Tetrahedron Lett. 1993, 34, 2665-2668; L. Saint-James, C. Lila, J. Z. Xu, L. Moreau, B. Pfeiffer, G. Eck, L. Pelsez, C. Rolando, M. Julia, Bull. Soc. Chim. France 1993, 130, 447-449; J. A. Wendt, P. J. Gauvreau, R. D. Bach, J. Am. Chem. Soc. 1994, 116, 9921-9926; D. L. J. Clive, Y. Tao, A. Khodabocus, Y. -J. Wu, A. G. Angoh, S. M. Bennett, C. N. Boddy, L. Bordeleau, D. Kellner, G. Kleiner, D. S. Middleton, C. J. Nichols, S. R. Richardson, P. G. Vernon, ibid. 1994, 116, 11275-11286.
9. (b) For studies on construction of the optically active quaternary carbon center in connection with the synthetic study of fredericamycin A, see: W. Trypke, A. Steigel, M. Braun, Synlett 1992, 827-829.
10. Our synthetic works for producing fredericamycin A, see: Y. Kita, R. Okunaka, T. Honda, M. Kondo, O. Tamura, Y. Tamura, Chem. Pharm. Bull. 1991, 39, 2106-2114; Y. Kita, H. Ueno, S. Kitagaki, K. Kobayashi, K. lio, S. Akai, J. Chem. Soc., Chem. Commun. 1994, 701-702 and references therein.
11. Our synthetic works for producing fredericamycin A, see: Y. Kita, R. Okunaka, T. Honda, M. Kondo, O. Tamura, Y. Tamura, Chem. Pharm. Bull. 1991, 39, 2106-2114; Y. Kita, H. Ueno, S. Kitagaki, K. Kobayashi, K. lio, S. Akai, J. Chem. Soc., Chem. Commun. 1994, 701-702 and references therein.
12. The single stereoisomer of each compound was depicted for easy understanding of the relative stereochemistry. Details of these syntheses will be published elsewhere.
13. Skeletal rearrangement of the epoxy alcohol derivatives, K. Maruoka, T. Ooi, S. Nagahara, H. Yamamoto, Tetrahedron 1991, 47, 6983-6998; K. Maruoka, J. Sato, H. Yamamoto, ibid. 1992, 48, 3749-3762 and references therein. C. M. Marson, A. J. Walker, J. Pickering, A. D. Hobson J. Org. Chem. 1993, 58, 5944-5951.
14. Skeletal rearrangement of the epoxy alcohol derivatives, K. Maruoka, T. Ooi, S. Nagahara, H. Yamamoto, Tetrahedron 1991, 47, 6983-6998; K. Maruoka, J. Sato, H. Yamamoto, ibid. 1992, 48, 3749-3762 and references therein. C. M. Marson, A. J. Walker, J. Pickering, A. D. Hobson J. Org. Chem. 1993, 58, 5944-5951.
15. Skeletal rearrangement of the epoxy alcohol derivatives, K. Maruoka, T. Ooi, S. Nagahara, H. Yamamoto, Tetrahedron 1991, 47, 6983-6998; K. Maruoka, J. Sato, H. Yamamoto, ibid. 1992, 48, 3749-3762 and references therein. C. M. Marson, A. J. Walker, J. Pickering, A. D. Hobson J. Org. Chem. 1993, 58, 5944-5951.
16. For synthetic studies of the spiro skeleton by acid catalyzed rearrangement of epoxy derivatives, see: R. D. Bach, M. W. Tubergen and R. C. Klix, Tetrahedron Lett. 1986, 27, 3565-3568 and references therein.
17. 2 column separation). In the case of cis-5a, the formation of the orthoester was not detected even using the TLC check.
18. For an example of epoxy acetates, see: J. M. Coxon, M. P. Hartshorn, D. N. Kirk, Tetrahedron 1964, 20, 2531-2545; 1964, 20, 2547-2552.
19. For an example of epoxy acetates, see: J. M. Coxon, M. P. Hartshorn, D. N. Kirk, Tetrahedron 1964, 20, 2531-2545; 1964, 20, 2547-2552.
20. 15 was not contained at all in the crude products of rearrangement reaction of trans-5a.
21. Very recently, we reported the stereoselective rearrangement of α,β-epoxyacylates in bicyclo-[n.3.0]alkanes (Tetrahedron Lett., 1995, 36, 3219-3222). In this case, only cis-α,β-epoxyacylates gave the spiro compounds in good yields via β-cleavage of the oxirane ring.
22. Compound 4 was prepared from 2-naphthaldehyde based on the synthetic procedure of a similar compound: P. McCloskey, J. Chem. Soc. 1965, 3811-3825; S. Mejer, Bull. Acta. Polon. Sci. Ser. Sci. Chim. 1962, 10, 469-473.
23. Compound 4 was prepared from 2-naphthaldehyde based on the synthetic procedure of a similar compound: P. McCloskey, J. Chem. Soc. 1965, 3811-3825; S. Mejer, Bull. Acta. Polon. Sci. Ser. Sci. Chim. 1962, 10, 469-473.
24. E. J. Corey, R. K. Bakshi, S. Shibata, C-P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925-7926.
25. 1H-NMR experiment. The spectra (500 MHz) of (-)-11 showed a double hydrogen resonance (95 to 5 ratio) of C9 aromatic H, although racemic 11 showed a clean separation of the two resonances for the two diastereomeric complexes.
26. K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-6137.
27. O. Mitsunobu, J. Kimura, K. Iiizumi, N. Yanagida, Bull. Chem. Soc. Jpn. 1976, 49, 510-513.
28. 1H-NMR analysis of the camphanoate ((-)-12).
29. 3.