Synthetic access to optically active isoflavans by using allylic substitution

Tetrahedron

Volumn 66, Issue 1, 2010, Pages 197-207

  Takashima, Yuji ^a   Kaneko, Yuki ^a   Kobayashi, Yuichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Allylic substitution; Asymmetric synthesis; Equol; Isoflavans; Picolinate; Sativan; Vestitol

Indexed keywords

ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; COPPER; EQUOL; ISOFLAVAN DERIVATIVE; PHENOL DERIVATIVE;

ARTICLE; ARYLATION; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; DIHYDROXYLATION; ENANTIOMER; HYDROBORATION; MITSUNOBU REACTION; PRIORITY JOURNAL; SUBSTITUTION REACTION; WITTIG REACTION;

EID: 70549095998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.116     Document Type: Article

References (62)

1. Veitch N.C. Nat. Prod. Rep. 24 (2007) 417-464
2. Paiva N.L., Oommen A., Harrison M.J., and Dixon R.A. Plant Cell Tissue Organ Cult. 38 (1994) 213-220
3. Tsukamoto S., Aburatani M., Yoshida T., Yamashita Y., El-beih A.A., and Ohta T. Biol. Pharm. Bull. 28 (2005) 2000-2002
4. Akashi T., Koshimizu S., Aoki T., and Ayabe S. FEBS Lett. 580 (2006) 5666-5670
5. (R)-isoflavans:
6. Matos F.J.d.A., Gottlieb O.R., and Andrade C.H.S. Phytochem. 14 (1975) 825-826
7. VanEtten H.D., Mattthews P.S., and Mercer E.H. Phytochemistry 22 (1983) 2291-2295
8. Alegrio L.V., Braz-Filho R., and Gottlieb O.R. Phytochemistry 28 (1989) 2359-2362 (S)-isoflavans
9. Kurosawa K., Ollis W.D., Redman B.T., and Sutherland I.O. J. Chem. Soc., Chem. Commun. (1968) 1263-1264
10. Kurosawa K., Ollis W.D., Redman B.T., and Sutherland I.O. J. Chem. Soc., Chem. Commun. (1968) 1265-1267
11. Kurosawa K., Ollis W.D., Redman B.T., Sutherland I.O., and Gottlieb O.R. Phytochemistry 17 (1978) 1413-1415
12. Kurosawa K., Ollis W.D., Redman B.T., Sutherland I.O., and Gottlieb O.R. Phytochemistry 17 (1978) 1417-1418
13. Piccinelli A.L., Fernandez M.C., Cuesta-Rubio O., Hernández I.M., De Simone F., and Rastrelli L. J. Agric. Food Chem. 53 (2005) 9010-9016
14. Marais J.P.J., Ferreira D., and Slade D. Phytochemistry 66 (2005) 2145-2176
15. Lamartiniere C.A. Am. J. Clin. Nutr. 71 (2000) 1705S-1707S
16. Adlercreutz H., Mousavi Y., Clark J., Hockerstedt K., Hamalainen E., Wahala K., Makela T., and Hase T. J. Steroid Biochem. Mol. Biol. 41 (1992) 331-337
17. Marrian G.F., and Haslewood G.A.D. Biochem. J. 26 (1932) 1226-1232
18. Chang Y.-C., and Nair M.G. J. Nat. Prod. 58 (1995) 1892-1896
19. Cf. isolation from woods: see Refs. 2d and 2e.
20. Borriello S.P., Setchell K.D., Axelson M., and Lawson A.M. J. Appl. Bacteriol. 58 (1985) 37-43
21. Sathyamoorthy N., and Wang T.T.Y. Eur. J. Cancer 33 (1997) 2384-2389
22. A similar study:. Morito K., Hirose T., Kinjo J., Hirakawa T., Okawa M., Nohara T., Ogawa S., Inoue S., Muramatsu M., and Masamune Y. Biol. Pharm. Bull. 24 (2001) 351-356
23. Muthyala R.S., Ju Y.H., Sheng S., Williams L.D., Doerge D.R., Katzenellenbogen B.S., Helferich W.G., and Katzenellenbogen J.A. Bioorg. Med. Chem. 12 (2004) 1559-1567
24. Schmitt E., Dekant W., and Stopper H. Toxicol. in Vitro 15 (2001) 433-439
25. Synthesis of racemic isoflavans:
26. Shih T.L., Wyvratt M.J., and Mrozik H. J. Org. Chem. 52 (1987) 2029-2033
27. Yoo S.-K., and Nahm K. Bull. Korean Chem. Soc. 28 (2007) 481-484
28. Gharpure S.J., Sathiyanarayanan A.M., and Jonnalagadda P. Tetrahedron Lett. 49 (2008) 2974-2978
29. Heemstra J.M., Kerrigan S.A., Doerge D.R., Helferich W.G., and Boulanger W.A. Org. Lett. 8 (2006) 5441-5443
30. Versteeg M., Bezuidenhoudt B.C.B., Ferreira D., and Swart K.J. J. Chem. Soc., Chem. Commun. (1995) 1317-1318
31. Versteeg M., Bezuidenhoudt B.C.B., and Ferreira D. Tetrahedron 55 (1999) 3365-3376
32. Wang X.-L., Hur H.-G., Lee J.H., Kim K.T., and Kim S.-I. Appl. Environ. Microbiol. 71 (2005) 214-219
33. Kiyotsuka Y., Acharya H.P., Katayama Y., Hyodo T., and Kobayashi Y. Org. Lett. 10 (2008) 1719-1722
34. Kiyotsuka Y., Katayama Y., Acharya H.P., Hyodo T., and Kobayashi Y. J. Org. Chem. 74 (2009) 1939-1951
35. Takashima Y., and Kobayashi Y. Tetrahedron Lett. 49 (2008) 5156-5158
36. Bernstein P.R., Snyder D.W., Adams E.J., Krell R.D., Vacek E.P., and Willard A.K. J. Med. Chem. 29 (1986) 2477-2483
37. Massad S.K., Hawkins L.D., and Baker D.C. J. Org. Chem. 48 (1983) 5180-5182
38. Delpiccolo C.M.L., Méndez L., Fraga M.A., and Mata E.G. J. Comb. Chem. 7 (2005) 331-344
39. 3 for the former and the latter are δ 1.61 and 1.31 ppm, respectively.
40. There still remains a possibility of a few % racemization at the aldehyde stage.
41. Pettetier J.D., and Poirier D. Tetrahedron Lett. 35 (1994) 1051-1054
42. Similar migrations:
43. Suzuki K., Katayama E., Matsumoto T., and Tsuchihashi G. Tetrahedron Lett. 25 (1984) 3715-3718
44. Versteeg M., Bezuidenhoudt B.C.B., and Ferreira D. Heterocycles 48 (1998) 1373-1394
45. Ono M., Ehara T., Yokoyama H., Ohtani N., Hoshino Y., and Akita H. Chem. Pharm. Bull. 53 (2005) 1259-1265
46. Ehara T., Tanikawa S., Ono M., and Akita H. Chem. Pharm. Bull. 55 (2007) 1361-1364
47. Wilkinson J.A., Raiber E.-A., and Ducki S. Tetrahedron 64 (2008) 6329-6333
48. Palmer A.M., Webel M., Scheufler C., Haag D., and Müller B. Org. Proc. Res. Dev. 12 (2008) 1170-1182
49. Filho R.B., Gottlieb O.R., Mourão A.P., Rocha A.I.D., and Oliveira F.S. Phytochemistry 14 (1975) 1454-1456
50. Miller R.W., and Spencer G.F. J. Nat. Prod. 52 (1989) 634-636
51. Bail J.-C.L., Champavier Y., Chulia A.-J., and Habrioux G. Life Sci. 66 (2000) 1281-1291
52. Yoon J.S., Sung S.H., Park J.H., and Kim Y.C. Arch. Pharm. Res. 27 (2004) 589-592
53. Paulis T.D., Kumar Y., Johansson L., Rämsby S., Florvall L., Hall H., Ängeby-Möller K., and Ögren S.-O. J. Med. Chem. 28 (1985) 1263-1269
54. Russell G.B., Sutherland O.R.W., Hutchins R.F.N., and Christmas P.E. J. Chem. Ecol. 4 (1978) 571-579
55. Yahara S., Ogata T., Saijo R., Konishi R., Yamahara J., Miyahara K., and Nohara T. Chem. Pharm. Bull. 37 (1989) 979-987
56. Nechepurenko I.V., Polovinka N.P., Sal'nikova O.I., Pokrovskii L.M., Komarova N.I., Salakhutdinov N.F., and Nechepurenko S.B. Chem. Nat. Comp. 43 (2007) 5-9
57. Zhao L.-J., Kwong C.K.-W., Shi M., and Toy P.H. Tetrahedron 61 (2005) 12026-12032
58. 1H NMR and TLC analyses and by mp.
59. Vaccaro W.D., Sher R., and Davis Jr. H.R. Bioorg. Med. Chem. 6 (1998) 1429-1437
60. Faure S., Piva-Le-Blanc S., Bertrand C., Pete J.-P., Faure R., and Piva O. J. Org. Chem. 67 (2002) 1061-1070
61. Albert J.S., Aharony D., Andisik D., Barthlow H., Bernstein P.R., Bialecki R.A., Dedinas R., Dembofsky B.T., Hill D., Kirkland K., Koether G.M., Kosmider B.J., Ohnmacht C., Palmer W., Potts W., Rumsey W., Shen L., Shenvi A., Sherwood S., Warwick P.J., and Russell K. J. Med. Chem. 45 (2002) 3972-3983
62. Hiroya K., Suzuki N., Yasuhara A., Egawa Y., Kasano A., and Sakamoto T. J. Chem. Soc., Perkin Trans. 1 (2000) 4339-4346