Titanocene(III) chloride mediated radical-induced synthesis of 3,4-dihydroisocoumarins: synthesis of (±)-hydrangenol, (±)-phyllodulcin, (±)-macrophyllol and (±)-thunberginol G

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11050-11057

  Mandal, Samir Kumar ^a   Roy, Subhas Chandra ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Dihydroisocoumarins; Natural products; Radical; Synthesis; Titanocene(III) chloride

Indexed keywords

HYDRANGENOL; ISOCOUMARIN DERIVATIVE; MACROPHYLLOL; PHYLLODULCIN; THUNBERGINOL G; TITANOCENE CHLORIDE; TITANOCENE DICHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION;

EID: 54549114162     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.075     Document Type: Article

References (59)

1. Nozawa K., Yamada M., Tsuda Y., Kawai K., and Nakajima S. Chem. Pharm. Bull. 29 (1981) 2689
2. ShimoJima Y., Shirai T., Baba T., and Hayashi H. J. Med. Chem. 28 (1885) 3
3. Fusetani N., Sugawar T., Matsunaga S., and Hirota H. J. Org. Chem. 56 (1991) 4971
4. Yoshikawa M., Uchida E., Chatani N., Kobayashi H., Naitoh Y., Okuno Y., Matsuda H., Yamahara J., and Murakami N. Chem. Pharm. Bull. 40 (1992) 3352
5. Yoshikawa M., Ueda T., Shimoda H., Murakami T., Yamahara J., and Matsuda H. Chem. Pharm. Bull. 47 (1999) 383
6. Umehara K., Matsumoto M., Nakamura M., Miyase T., Kuroyanagi M., and Noguchi H. Chem. Pharm. Bull. 48 (2000) 566
7. Kongsaeree P., Prabpai S., Sriubolmas N., Vongvein C., and Wiyakrutta S. J. Nat. Prod. 66 (2003) 709
8. Kokubun T., Veitch N.C., Bridge P.D., and Simmonds M.S.J. Phytochemistry 62 (2003) 779
9. Zidorn C., Lohwasser U., Pschorr S., Salvenmoser D., Ongania K.-H., Ellmerer E.P., Börner A., and Stuppner H. Phytochemistry 66 (2005) 1691
10. Jiao P., Gloer J.B., Campbell J., and Shearer C.A. J. Nat. Prod. 69 (2006) 612
11. Asahina Y., and Asano J. Chem. Ber. 62B (1929) 171
12. Asahina Y., and Asano J. Chem. Ber. 63B (1930) 429
13. Hashimoto T., Tori M., and Asakawa Y. Phytochemistry 26 (1987) 3323
14. Yoshikawa M., Matsuda H., Shimoda H., Shimada H., Harada E., Naitoh Y., Miki A., Yamahara J., and Murakami N. Chem. Pharm. Bull. 44 (1996) 1440
15. Matsuda H., Shimoda H., and Yoshikawa M. Bioorg. Med. Chem. 7 (1999) 1445
16. Yamahara J., Matsuda H., Shimoda H., Ishikawa H., Kawamori S., Wariishi N., Harada E., Murakami N., and Yoshikawa M. Yakugaku Zasshi 114 (1994) 401
17. Yamahara J., Miki A., Tsukamoto K., Ueno A., Murakami N., and Yoshikawa M. Nat. Med. 49 (1995) 84
18. Matsuda H., Shimoda H., Yamahara J., and Yoshikawa M. Bioorg. Med. Chem. Lett. 8 (1998) 215
19. Shin W., Kim S.J., Shin J.M., and Kim S.H. J. Med. Chem. 38 (1995) 4325
20. Watanabe M., Sahara M., Kubo M., Furukawa S., Billedeau R.J., and Snieckus V. J. Org. Chem. 49 (1984) 742
21. Fu P.P., Unruh L.E., Miller D.W., Huang L.W., and Yang D.T.C. J. Org. Chem. 50 (1985) 1259
22. Regan A.C., and Staunton J. J. Chem. Soc., Chem. Commun. (1987) 520
23. Broady S.D., Rexhausen J.E., and Thomas E.J. J. Chem. Soc., Chem. Commun. (1991) 708
24. Ward R.A., and Procter G. Tetrahedron 51 (1995) 12301
25. McNicholas C., Simpson T.J., and Willett N.J. Tetrahedron Lett. 37 (1996) 8053
26. Salvadori P., Superchi S., and Minutolo F. J. Org. Chem. 61 (1996) 4190 and references therein
27. Uchida K., Watanabe H., and Kitahara T. Tetrahedron 54 (1998) 8975
28. Tahara N., Fukuda T., and Iwao M. Tetrahedron Lett. 45 (2004) 5117
29. Clayden J., Stimson C.C., Helliwell M., and Keenan M. Synlett (2006) 873
30. Günes M., and Speicher A. Tetrahedron 59 (2003) 8799
31. Kessar S.V., Singh P., Vohra R., Kour N.P., and Venugopal D. J. Org. Chem. 57 (1992) 6716
32. Mali R.S., and Babu K.N. J. Indian Inst. Sci. 81 (2001) 103
33. Takeuchi N., Murase M., Ochi K., and Tobinaga S. J. Chem. Soc., Chem. Commun. (1976) 820
34. Takeuchi N., Ochi K., Murase M., and Tobinaga S. J. Chem. Soc., Chem. Commun. (1980) 593
35. Fitzgerald J.J., Pagano A.R., Sakoda V.M., and Olofson R.A. J. Org. Chem. 59 (1994) 4117
36. Mandal P.K., Maiti G., and Roy S.C. J. Org. Chem. 63 (1998) 2829
37. Roy S.C., Rana K.K., and Guin C. J. Org. Chem. 67 (2002) 3242
38. Banerjee B., and Roy S.C. Synthesis (2005) 2913
39. Banerjee B., and Roy S.C. Eur. J. Org. Chem. (2006) 489
40. Jana S., Guin C., and Roy S.C. Tetrahedron Lett. 45 (2004) 6575
41. Jana S., Guin C., and Roy S.C. J. Org. Chem. 70 (2005) 8252
42. Jana S., Guin C., and Roy S.C. Tetrahedron Lett. 46 (2005) 1155
43. Mandal S.K., Jana S., and Roy S.C. Tetrahedron Lett. 46 (2005) 6115
44. Mandal S.K., and Roy S.C. Tetrahedron Lett. 47 (2006) 1599
45. Jana S., and Roy S.C. Tetrahedron Lett. 47 (2006) 5949
46. RajanBabu T.V., and Nugent W.A. J. Am. Chem. Soc. 116 (1994) 986 and references cited therein
47. Cuerva J.M., Justicia J., Oller-López J.L., and Oltra J.E. Top. Curr. Chem. 264 (2006) 63
48. Barrero A.F., Quílez del Moral J.F., Sánchez E.M., and Arteaga J.F. Eur. J. Org. Chem. (2006) 1627
49. Gansäuer A. Synlett (1998) 801
50. Gansäuer A., and Bluhm H. Chem. Commun. (1998) 2143
51. Gansäuer A., Lauterbach T., Bluhm H., and Noltemeyer M. Angew. Chem., Int. Ed. 38 (1999) 2909
52. Gansäuer A., Lauterbach T., and Narayan S. Angew. Chem., Int. Ed. 42 (2003) 5556
53. Journet M., and Malacria M. J. Org. Chem. 59 (1994) 718
54. Devin P., Festerbank L., and Malacria M. J. Org. Chem. 63 (1998) 6764
55. For preliminary communication see:. Mandal S.K., and Roy S.C. Tetrahedron Lett. 48 (2007) 4131
56. [Corrigendum:. Mandal S.K., and Roy S.C. Tetrahedron Lett. 48 (2007) 6225 ]
57. 2TiCl-mediated reaction of activated bromocompounds with aldehydes has also been reported at the same time by. Barrero A.F., Herrador M.M., Quílez del Moral J.F., Arteaga P., Akssira M., EI Hanbali F., Arteaga J.F., Diéguez H.R., and Sánchez E.M. J. Org. Chem. 72 (2007) 2251
58. Rosales A., Oller-Lopez J.L., Justicia J., Gansäuer A., Oltra J.E., and Cuerva J.M. Chem. Commun. (2004) 2628
59. Kanakam C.C., Mani N.S., Ramanathan H., and Subba Rao G.S.R. J. Chem. Soc., Perkin Trans. 1 (1989) 1907