Stereoselective synthesis of (-)-blepharocalyxin D

Tetrahedron

Volumn 63, Issue 26, 2007, Pages 5797-5805

  Ko, Haye Min ^a   Lee, Dong Gil ^a   Kim, Min Ah ^a   Kim, Hak Joong ^a   Park, Jaejoon ^b   Lah, Myoung Soo ^b   Lee, Eun ^a  

^a Seoul National University   (South Korea)

^b Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALPINIA BLEPHAROCALYX EXTRACT; BLEPHAROCALYXIN D; CYTOTOXIC AGENT; PLANT EXTRACT; UNCLASSIFIED DRUG;

ALPINIA; ARTICLE; CYCLIZATION; CYTOTOXICITY; DRUG ISOLATION; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

ALPINIA BLEPHAROCALYX;

EID: 34248662084     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.028     Document Type: Article

References (32)

1. Kadota S., Prasain J.K., Li J.X., Basnet P., Dong H., Tani T., and Namba T. Tetrahedron Lett. 37 (1996) 7283-7286
2. Prasain J.K., Tezuka Y., Li J.X., Tanaka K., Basnet P., Dong H., Namba T., and Kadota S. Tetrahedron 53 (1997) 7833-7842
3. Prasain J.K., Li J.-X., Tezuka Y., Tanaka K., Basnet P., Dong H., Namba T., and Kadota S. J. Nat. Prod. 61 (1998) 212-216
4. Gewali M.B., Tezuka Y., Banskota A.H., Ali M.S., Saiki I., Dong H., and Kadota S. Org. Lett. 1 (1999) 1733-1736
5. Tezuka Y., Ali M.S., Banskota A.H., and Kadota S. Tetrahedron Lett. 41 (2000) 5903-5907
6. Tezuka Y., Gewali M.B., Ali M.S., Banskota A.H., and Kadota S. J. Nat. Prod. 64 (2001) 208-213
7. Ali M.S., Tezuka Y., Awale S., Banskota A.H., and Kadota S. J. Nat. Prod. 64 (2001) 289-293
8. Ali M.S., Tezuka Y., Banskota A.H., and Kadota S. J. Nat. Prod. 64 (2001) 491-496
9. For further references on some related compounds, see:
10. Kikuzaki H., and Nakatani N. Phytochemistry 43 (1996) 273-277
11. Shin D., Kinoshita K., Koyama K., and Takahashi K. J. Nat. Prod. 65 (2002) 1315-1318
12. Sekiguchi M., Shigemori H., Ohsaki A., and Kobayashi J. J. Nat. Prod. 65 (2002) 375-376
13. Jang D.S., Park E.J., Hawthorne M.E., Vigo J.S., Graham J.G., Cabieses F., Santarsiero B.D., Mesecar A.D., Fong H.H.S., Mehta R.G., Pezzuto J.M., and Kinghorn A.D. J. Agric. Food Chem. 50 (2002) 6330-6334
14. Tian X., Jaber J.J., and Rychnovsky S.D. J. Org. Chem. 71 (2006) 3176-3183
15. As far as we know, blepharocalyxin D (1) is the only natural product known to possess a 2,8-dioxabicyclo[4.4.0]decane core.
16. There is one reference claiming to be a model study for synthesis of blepharocalyxin D (1):. Li W., Mead K.T., and Smith L.T. Tetrahedron Lett. 44 (2003) 6351-6353
17. Ko H.M., Lee D.G., Kim M.A., Kim H.J., Park J., Lah M.S., and Lee E. Org. Lett. 9 (2007) 141-144
18. Barry C.S.J., Crosby S.R., Harding J.R., Hughes R.A., King C.D., Parker G.D., and Willis C.L. Org. Lett. 5 (2003) 2429-2432
19. Hanawa H., Uraguchi D., Konishi S., Hashimoto T., and Maruoka K. Chem.-Eur. J. 9 (2003) 4405-4413
20. For extensive use of (O)-acetylmandelate NMR correlation, see:. Lee E., Lee Y.R., Moon B., Kwon O., Shim M.S., and Yun J.S. J. Org. Chem. 59 (1994) 1444-1456
21. Crosby S.R., Harding J.R., King C.D., Parker G.D., and Willis C.L. Org. Lett. 4 (2002) 577-580
22. Kim E.J., and Ko S.Y. Bioorg. Med. Chem. 13 (2005) 4103-4112
23. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168-8179
24. For a recent discussion on oxonia-Cope rearrangement, see:. Jasti R., Anderson C.D., and Rychnovsky S.D. J. Am. Chem. Soc. 127 (2005) 9939-9945
25. For an example of similar β-alkoxyvinyl ketone radical cyclization, see:. Lee E., Kim H.J., and Jang W.S. Bull. Korean Chem. Soc. 25 (2004) 1609-1610
26. Li D., Shi F., Peng J., Guo S., and Deng Y. J. Org. Chem. 69 (2004) 3582-3585
27. There are two stereoisomers possible for 18 and 20, and four possible isomers for the cyclic acetal from 18. Chromatographic and spectroscopic analyses suggested the presence of a major isomer for each of these compounds, but this point was not further elaborated as the second Prins cyclization provided a single stereoisomer 21.
28. Cloninger M.J., and Overman L.E. J. Am. Chem. Soc. 121 (1999) 1092-1093
29. For more discussions on Prins-pinacol reactions, see:. Overman L.E., and Pennington L.D. J. Org. Chem. 68 (2003) 7143-7157
30. Baudin J.B., Hareau G., Julia S.A., and Ruel O. Tetrahedron Lett. 32 (1991) 1175-1178
31. For a recent example of use of lithium alkanethiolate in hot HMPA for aromatic ether demethylation, see:. Nakatani M., Nakamura M., Suzuki A., Inoue M., and Katoh T. Org. Lett. 4 (2002) 4483-4486
32. In the NMR spectra provided by Prof. Kadota, all the signals exhibited by the synthetic sample of 1 were present, but the natural sample clearly contained relatively large amount of impurities.