Citation: Liu Liangyan, Feng Tao, Li Zhenghui, Liu Jikai. Four New 2, 5-Disubstituted Furan Vicinal Diols from the Fungus Ceriporia alachuana[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1577-1581. doi: 10.6023/cjoc201701016 shu

Four New 2, 5-Disubstituted Furan Vicinal Diols from the Fungus Ceriporia alachuana

Liu Liangyan ^a ,
Feng Tao ^b ,
Li Zhenghui ^b ,
Liu Jikai ^b,*,,

a.
College of Agronomy and Biotechnology, Yunnan Agricultural University, Kunming 650201
b.
School of Pharmaceutical Sciences, South-Central University for Nationalities, Wuhan 430074

Corresponding author: Liu Jikai, jkliu@mail.kib.ac.cn
Received Date: 7 January 2017
Revised Date: 20 January 2017

Fund Project: the National Natural Science Foundation of China 81561148013the National Natural Science Foundation of China 21502167

Figures(6)

Four new closely related vicinal diols, (1R, 2R)-1-(5-(pent-4-en-1-yl)furan-2-yl)propane-1, 2-diol (1), (1S, 2R)-1-(5-(pent-4-en-1-yl)furan-2-yl)propane-1, 2-diol (2), (1R, 2R)-1-(5-pentylfuran-2-yl)propane-1, 2-diol (3) and (1R, 2S)-1-(5-pen-tylfuran-2-yl)propane-1, 2-diol (4), were isolated from the cultures of the fungus Ceriporia alachuana. Their structures and absolute configurations were totally determined by spectroscopic means, chemical method (forming di-O-isopropylidene derivative) and Mo₂(OAc)₄ induced circular dichroism (ICD) experiments.
- vicinal diols,
- Ceriporia alachuana,
- induced circular dichroism (ICD),
- dimolybdenum tetraacetate
1. [1]
  Takatsuto, S.; Ikekawa, N. J. Chem. Soc., Perkin Trans. 1 1983, 2133.
2. [2]
  Thadepalli, H.; Chuah, S. K.; Iskandar, L.; Gollapudi, S. Int. J. Antimicrob. Agents 2002, 20, 180. doi: 10.1016/S0924-8579(02)00176-0
3. [3]
  Nakakita, Y.; Nakagawa, M.; Sakai, H. J. Antibiot. 1980, 33, 514. doi: 10.7164/antibiotics.33.514
4. [4]
  Roush, W. R.; Hartz, R. A.; Gustin, D. J. J. Am. Chem. Soc. 1999, 121, 1990. doi: 10.1021/ja984229e
5. [5]
  Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. doi: 10.1021/cr00032a009
6. [6]
  Harada, N.; Nakanishi, K. Acc. Chem. Res. 1972, 5, 257. doi: 10.1021/ar50056a001
7. [7]
  Nakanishi, K.; Berova, N. Circular Dichroism: Principles and Applications, 2nd ed., Ed.: Woody, R. W., Weily-VCH, New York, 2000, Chapter 12.
8. [8]
  Bukhari, S. T. K.; Guthrie, R. D.; Scott, A. I.; Wrixon, A. D. Chem. Commun. 1968, 24, 1580.
9. [9]
  Bukhari, S. T. K.; Guthrie, R. D.; Scott, A. I.; Wrixon, A. D. Tetrahedron 1970, 26, 3653. doi: 10.1016/S0040-4020(01)92943-6
10. [10]
  Scott, I.; Wrixon, A. D. Chem. Commun. 1969, 20, 1184.
11. [11]
  Nakanishi, K.; Schooley, D. A.; Koreeda, M.; Dillon, J. Chem. Commun. 1971, 20, 1235.
12. [12]
  Dillon, J.; Nakanishi, K. J. Am. Chem. Soc. 1974, 96, 4055. doi: 10.1021/ja00819a076
13. [13]
  Dillon, J.; Nakanishi, K. J. Am. Chem. Soc. 1975, 97, 5409. doi: 10.1021/ja00852a015
14. [14]
  Frelek, J.; Ikekawa, N.; Takatsuto, S.; Snatzke, G. Chirality 1997, 9, 578. doi: 10.1002/(ISSN)1520-636X
15. [15]
  Bari, L. D.; Pescitelli, G.; Pratelli, C.; Pini, D.; Salvadori, P. J. Org. Chem. 2001, 66, 4819. doi: 10.1021/jo010136v
16. [16]
  Xu, L. X.; He, Z. X.; Xue, J. H.; Chen, X. P.; Wei, X. Y. J. Nat. Prod. 2010, 73, 885. doi: 10.1021/np900853n
17. [17]
  Liu, J.; Du, D.; Si, Y. K.; Lv, H. N.; Wu, X. F.; Li, Y.; Liu, Y. Y.; Yu, S. S. Chin. J. Org. Chem. 2010, 30, 1270.
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