Efficient synthesis of (±)-, (+)-, and (-)-conduritol C via palladium(II)-catalyzed 1,4-diacetoxylation in combination with enzymatic hydrolysis

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9339-9341

  Yoshizaki, Hiroki ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

5,6 ISOPROPYLENDIOXY 1,3 CYCLOHEXADIENE; ACETIC ACID DERIVATIVE; ALKADIENE; CONDURITOL C; PALLADIUM; UNCLASSIFIED DRUG;

ACETYLATION; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032509263     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981281k     Document Type: Article

References (26)

1. (a) Külber, K. Arch. Pharm. 1908, 346, 620.
2. (b) Kern, W.; Fricke, W. Pharm. Zentralhalle 1939, 80, 349-352.
3. (c) Manni, P. E.; Sinsheimer, J. E. J. Pharm. Sci. 1965, 54, 1541.
4. (d) Dominguez, X. A.; Marroquin, J.; Olguin, L. M.; Morales, F.; Valdez, V. Phytochemistry 1974, 13, 2617-2618.
5. (a) Legler, G.; Bause, E. Carbohydr. Res. 1973, 28.
6. (b) Legler, G.; Lotz, W. Physiol. Chem. 354, 1973, 243.
7. (c) Umezawa, S. Adv. Carbohydr. Chem. Biochem. 1974, 30, 111-225.
8. (d) Atsumi, S.; Umezawa, K.; Iinuma, H.; Nakamura, H.; Iitaka, Y. J. Antibiot. 1989, 43, 49-53.
9. For excellent reviews on preparation of conduritols, see: (a) BalcI, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron 1990, 46, 3715-3742. (b) Hudlicky, T.; Reed, J. W. In Advances In Asymmetric Synthesis; JAI Press Inc.: London, 1995; Vol. 1, p 271-312. (c) BalcI, M. Pure Appl. Chem. 1997, 69, 97-104.
10. For excellent reviews on preparation of conduritols, see: (a) BalcI, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron 1990, 46, 3715-3742. (b) Hudlicky, T.; Reed, J. W. In Advances In Asymmetric Synthesis; JAI Press Inc.: London, 1995; Vol. 1, p 271-312. (c) BalcI, M. Pure Appl. Chem. 1997, 69, 97-104.
11. For excellent reviews on preparation of conduritols, see: (a) BalcI, M.; Sütbeyaz, Y.; Seçen, H. Tetrahedron 1990, 46, 3715-3742. (b) Hudlicky, T.; Reed, J. W. In Advances In Asymmetric Synthesis; JAI Press Inc.: London, 1995; Vol. 1, p 271-312. (c) BalcI, M. Pure Appl. Chem. 1997, 69, 97-104.
12. Le Drian, C.; Vieira, E.; Vogel, P. Helv. Chim. Acta 1989, 72, 338-347.
13. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
14. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
15. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
16. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
17. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
18. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
19. For more recent examples, see: (a) Johnson, C. R.; Plé, P. A.; Adams, J. P. J. Chem. Soc., Chem. Commun. 1991, 1006-1007. (b) Dumortier, L.; Liu, P.; Dobbelaere, S.; Van der Eycken, J.; Vandewalle, M. Synlett 1992, 243-245. (c) Patti, A.; Sanfilippo, C.; Piatteri, M.; Nicolosi, G. Tetrahedron: Asymmetry 1996, 7, 2665-2670 (conduritol C and D). (d) Carless, H. A. J.; Oak, O. Z. J. Chem. Soc., Chem. Commun. 1991, 61-62. (e) McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1991, 56, 5010-5012. (f) Carless, H. A. J. J. Chem. Soc., Chem. Commun. 1992, 234-235. (g) Innes, J. E.; Edwards, P. J.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 795-796 ((+)-D-conduritol B).
20. (a) Yang, N. C.; Chen, M.-J.; Chen, P. J. J. Am. Chem. Soc. 1984, 106, 7310-7315.
21. (b) Ramesh, K.; Wolfe, M. S.; Lee, Y.; Velde, D. V.; Borchardt, R. T. J. Org. Chem. 1992, 57, 5861-5868.
22. (a) Bäckvall, J. E. In Organometallic Reagents in Organic Synthesis; Academic: London, 1994; p 81-97.
23. (b) Bäckvall, J. E.; Byström, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619-4631.
24. (c) Bäckvall, J. E.; Hopkins, R. B.; Grennberg, H.; Mader, M.; Awasthi, A. K. J. Am. Chem. Soc. 1990, 112, 5160.
25. Prelog, V. Pure Appl. Chem. 1964, 9, 119-130.
26. Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. V. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665.