SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 10: 2035 - 2039

DOI: https://doi.org/10.6023/cjoc201405038

Articles

Practical Synthesis of the C(11)～C(21) Fragment of Geldanamycin

  • Li Yongqiang ,
  • Yan Rui ,
  • Bian Chuancai ,
  • Zhang Zhi ,
  • Liu Di ,
  • Yu Xiaoming
Expand
  • State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050

Received date: 2014-05-29

  Revised date: 2014-06-05

  Online published: 2014-06-16

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272279).

Fold

Abstract

The C(11)～C(21) fragment of benzoquinone ansamycin geldanamycin was synthesized in 10 steps and 24% overall yield from known lactone 5, which was prepared from tri-O-acetyl-D-glucal in 3 steps. The key steps included an α-methylenation of lactone 5, followed by a substance induced facial selective hydrogenation.

Key words： geldanamycin; chiral γ-lactone; asymmetric synthesis

Cite this article

Li Yongqiang , Yan Rui , Bian Chuancai , Zhang Zhi , Liu Di , Yu Xiaoming . Practical Synthesis of the C(11)～C(21) Fragment of Geldanamycin[J]. Chinese Journal of Organic Chemistry, 2014 , 34(10) : 2035 -2039 . DOI: 10.6023/cjoc201405038

References

[1] DeBoer, C.; Meulman, P.; Wnuk, R.; Peterson, D. J. Antibiot. 1970, 23, 442.
[2] Whitesell, L.; Mimnaugh, E. G.; De Costa, B.; Myers, C. E.; Neckers, L. M. Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 8324.
[3] Garcia-Carbonero, R.; Carnero, A.; Paz-Ares, L. Lancet Oncol. 2013, 14, e358.
[4] (a) Franke, J.; Eichner, S.; Zeilinger, C.; Kirschning, A. Nat. Prod. Rep. 2013, 30, 1299.
(b) Kitson, R. R.; Moody, C. J. J. Org. Chem. 2013, 78, 5117.
(c) Kim, T.; Keum, G.; Pae, A. N. Expert Opin. Ther. Pat. 2013, 23, 919.
[5] Andrus, M. B.; Meredith, E. L.; Hicken, E. J.; Simmons, B. L.; Glancey, R. R.; Ma, W. J. Org. Chem. 2003, 68, 8162.
[6] Qin, H.-L.; Panek, J. S. Org. Lett. 2008, 10, 2477.
[7] (a) Horneff, T.; Bach, T. Synlett 2008, 2969.
(b) Hampel, T.; Neubauer, T.; van Leeuwen, T.; Bach, T. Chem.- Eur. J. 2012, 18, 10382.
[8] Bian, C.; Yan, R.; Yu, X. Tetrahedron 2014, 70, 2982.
[9] (a) Nakata, M.; Osumi, T.; Ueno, A.; Kimura, T.; Tamai, T.; Tatsuta, K. Tetrahedron Lett. 1991, 32, 6015.
(b) Canova, S.; Bellosta, V.; Bigot, A.; Mailliet, P.; Mignani, S.; Cossy, J. Org. Lett. 2007, 9, 145.
(c) Carter, K. D.; Panek, J. S. Org. Lett. 2004, 6, 55.
[10] Lee, J.; Lewin, N. E.; Acs, P.; Blumberg, P. M.; Marquez, V. E. J. Med. Chem. 1997, 40, 1560.

Options
Outlines

/

〈 〉