Novel and stereocontrolled asymmetric synthesis of a new naturally occurring styryllactone, (+)-cardiobutanolide

Tetrahedron Letters

Volumn 47, Issue 9, 2006, Pages 1371-1374

  Matsuura, Daisuke ^a   Takabe, Kunihiko ^a   Yoda, Hidemi ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

Author keywords

Cardiobutanolide; Glucuronolactone; Grignard addition; Stereoselective reduction; Styryllactone

Indexed keywords

BUTYROLACTONE; CARDIOBUTANOLIDE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; GRIGNARD REACTION; STEREOCHEMISTRY;

GONIOTHALAMUS;

EID: 31444435075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.113     Document Type: Article

References (43)

1. For a review on styryllactones from Goniothalamus species, see: M.A. Blàzquez, A. Bermejo, M.C. Zafra-Polo, and D. Cortes Phytochem. Anal. 10 1999 161
2. F.Q. Alali, X.X. Liu, and J.L. McLaughlin J. Nat. Prod. 62 1999 504
3. M.C. Zafra-Polo, B. Figadère, T. Gallardo, J.R. Tormo, and D. Cortés Phytochemistry 48 1998 1087
4. A. Cavé, B. Figadère, A. Laurens, and D. Cortés Prog. Chem. Org. Nat. Prod. 70 1997 81
5. On the cytotoxic activity and other bioactivity of styryllactones, see: H.B. Mereyala, and M. Joe Curr. Med. Chem.: Anti-Cancer Agents 1 2001 293
6. For some recent examples; K.R. Prasad, and S.L. Gholap Synlett 2005 2260
7. V. Popsavin, S. Grabež, M. Popsavin, I. Krstić, V. Kojić, G. Bogdanović, and V. Divjaković Tetrahedron Lett. 45 2004 9409
8. E. Peris, A. Cavé, E. Estornell, M.C. Zafra-Polo, B. Figadère, D. Cortes, and A. Bermejo Tetrahedron 58 2002 1335
9. G.S.C. Srikanth, U.M. Krishna, and G.K. Trivedi Tetrahedron Lett. 43 2002 5471
10. J.M. Harris, and G.A. O'Doherty Tetrahedron 57 2001 5161
11. Y.-L. Su, C.-S. Yang, S.-J. Teng, G. Zhao, and Y. Ding Tetrahedron 57 2001 2147
12. J.-P. Surivet, and J.-M. Vatele Tetrahedron 55 1999 13011
13. H.B. Mereyala, R.R. Gadikota, M. Joe, S.K. Arora, S.G. Datidar, and S. Agarwal Bioorg. Med. Chem. 7 1999 2095
14. R. Bruns, A. Wenicke, and P. Köll Tetrahedron 55 1999 9793
15. M. Tsubuki, K. Kanai, H. Nagase, and T. Honda Tetrahedron 55 1999 2493
16. W.-P. Chen, and S.M. Roberts J. Chem. Soc., Perkin Trans. 1 1999 103
17. X.-H. Yi, Y. Meng, X.-G. Hua, and C.-J. Li J. Org. Chem. 63 1998 7472
18. C. Cagnolini, M. Ferri, P.R. Jones, P.J. Murphy, B. Ayres, and B. Cox Tetrahedron 53 1997 4815
19. C. Mukai, S. Hirai, I.J. Km, M. Kido, and M. Hanaoka Tetrahedron 52 1996 6547
20. T.K.M. Shing, H.C. Tsui, and Z.H. Zhou J. Org. Chem. 60 1995 3121
21. Z.-C. Yang, and W.-S. Zhou Tetrahedron 51 1995 1429
22. T. Gracza, and V. Jäger Synthesis 1994 1359
23. J. Ye, R.K. Bhatt, and R.J.R. Falck Tetrahedron Lett. 34 1993 8007
24. P.J. Murphy, and S.T. Dennison Tetrahedron 49 1993 6695
25. K.R.C. Prakash, and S.P. Rao Tetrahedron 49 1993 1505
26. T.K.M. Shine, H.C. Tsui, and Z.H. Zhou Tetrahedron 48 1992 8659 Absolute configurations of these styryl groups are in accord with those of all suggested biogenetic precursors and allowed to propose the absolute configurations of related cytotoxic styryllactones and strucutures of potential biosynthetic intermediates not identified so far, see: Ref. 4q
27. A. Hisham, M. Toubi, W. Shuaily, M.D. Ajitha Bai, and Y. Fujimoto Phytochemistry 62 2003 597
28. P. Ruiz, J. Murga, M. Carda, and J.A. Marco J. Org. Chem. 70 2005 713
29. H. Yoda, Y. Nakaseko, and K. Takabe Tetrahedron Lett. 45 2004 4217
30. H. Yoda, Y. Nakaseko, and K. Takabe Synlett 2002 1532
31. M.J. Robins, and J.S. Wilson J. Am. Chem. Soc. 103 1981 932
32. Similar carbohydrate-derived starting materials were also applied to the total synthesis of related styryllactones. For example, see: Ref. 4o. Direct treatment of 9 according to the following reaction sequence cited in Scheme 1 yielded only intractable materials at the final step of acetonide-deprotection.
33. It is not necessarily to determine the absolute configuration at this anomer center, since the lactol function should be oxidized to the corresponding lactone at the final stage for the synthesis of 1.
34. H. Yoda, M. Mizutani, and K. Takabe Heterocycles 48 1998 479
35. H. Yoda, M. Mizutani, and K. Takabe Synlett 1998 855
36. The absolute configuration of the newly created stereogenic center of 13b was easily characterized to be R after derivatization via the mesylate 19 to the corresponding cis-epoxide 20 as shown below.
37. b) was 4.38 Hz, which indicates the epoxide in 20 occupy the cis-relation; see: K. Tanaka, H. Horiuchi, and H. Yoda J. Org. Chem. 54 1989 63
38. M. Shimagaki, T. Maeda, Y. Matsuzaki, I. Mori, T. Nakata, and T. Oishi Tetrahedron Lett. 25 1984 4775
39. Compound 13a was also estimated to have the same configuration based on the similarity of its spectral data to those of 13b.
40. When reduction of the labile hemiketal intermediate derived from 12b was carried out under slightly different conditions (change of the reduction temperature from -40 to -20°C), the reaction occurred with unsatisfactory stereoselectivity to give the mixture of the two diastereomers (13b : 14b = 86:14). It is consequently apparent that stereochemical outcome in these reactions strongly depends on the two factors; (a) steric bulkiness of the protecting groups in 12 and (b) reduction temperature of the hemiketal intermediates. These results can be explained that the reaction would proceed simply in terms of the thermodynamically more stable Cram's non-chelation transition structure.
41. The absolute R-configuration of the generated stereogenic center was determined unambiguously based on its spectral data of synthetic (+)-1.
42. 3-mediated six-membered metal-chelate structure due to the bottom-face shielding effect of the three large functional groups described below.
43. The same type of transition metal halide-promoted six-membered chelating reactions have already been demonstrated in this laboratory with high stereoselectivity; see: H. Yoda, T. Nakajima, and K. Takabe Tetrahedron Lett. 37 1996 5531