Indoxamycin家族分子的合成研究进展
收稿日期: 2015-01-05
修回日期: 2015-02-03
网络出版日期: 2015-01-05
基金资助
国家自然科学基金(Nos. 21472167, 21202144)、新博士点教师基金(No. 20120101120087)资助项目.
Synthetic Progress of Indoxamycin Family
Received date: 2015-01-05
Revised date: 2015-02-03
Online published: 2015-01-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21472167, 21202144) and the Research Fund For the Doctoral Program of Higher Education of China (No. 20120101120087).
Indoxamycins A～F是从海洋放线菌中分离得到的一类聚酮化合物, 它们均含有空间拥挤的[5,5,6]三环类笼状结构和6个连续的手性中心. 前期活性研究表明, indoxamycins A和F对HT-29肿瘤细胞株具有显著的生长抑制活性. 该综述总结了Carreira和丁寒锋两个小组在此家族天然产物全合成中取得的进展情况.
关键词： indoxamycins; 烯炔; 重排; 串联反应; 全合成
何驰 , 丁寒锋 . Indoxamycin家族分子的合成研究进展[J]. 有机化学, 2015 , 35(4) : 760 -769 . DOI: 10.6023/cjoc201501002
Indoxamycins A～F represent a novel class of polyketides isolated from the salin cultures of actinomycetes, which contain a common sterically congested [5,5,6] tricyclic cage-like structure featuring six contiguous stereogenic centers. Indoxamycins A and F were reported to exhibit significant growth-inhibition activity against HT-29 tumor cell lines. This review summarizes the synthetic progress towards indoxamycin family members both by the Carreira and Ding groups.
Key words： indoxamycins; enynes; rearrangement; tandem reaction; total synthesis
[1] Fenical, W.; Jensen, P. R. Nat. Chem. Biol. 2006, 2, 666.
[2] Sato, S.; Iwata, F.; Mukai, T.; Yamada, S.; Takeo, J.; Abe, A.; Kawahara, H. J. Org. Chem. 2009, 74, 5502.
[3] (a) Jeker, O. F.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3474.
(b) Jeker, O. F. Ph.D. Dissertation, ETH, Zurich (Switzerland), 2013.
[4] (a) He, C.; Zhu, C.; Dai, Z.; Tseng, C.-C.; Ding, H. Angew. Chem., Int. Ed. 2013, 52, 13256.
(b) He, C.; Zhu, C.; Ding, H. Synlett 2014, 25, 1487.
(c) He, C.; Zhu, C.; Wang, B. N.; Ding, H. Chem. Eur. J. 2014, 20, 15053.
[5] For reviews on tandem reaction, see:
(a) Bunce, R. A. Tetrahedron 1995, 51, 13103.
(b) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
(c) Padwa, A. Pure Appl. Chem. 2004, 76, 1933.
[6] For selected enantioselective Alder-ene reactions, see:
(a) Trost, B. M.; Czeskis, B. A. Tetrahedron Lett. 1994, 35, 211.
(b) Goeke, A.; Sawamura, M.; Kuwano, R.; Ito, Y. Angew. Chem., Int. Ed. 1996, 35, 662.
(c) Hatano, M.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 2001, 40, 249.
(d) Hatano, M.; Mikami, K. Org. Biomol. Chem. 2003, 1, 3871.
(e) Hatano, M.; Mikami, K. J. Am. Chem. Soc. 2003, 125, 4704.
(f) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5767.
[7] (a) Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sato, F. J. Am. Chem. Soc. 1995, 117, 3881.
(b) Yatsumonji, Y.; Nishimura, T.; Tsubouchi, A.; Noguchi, K.; Takeda, T. Chem. Eur. J. 2009, 15, 2680.
[8] (a) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494.
(b) Kende, A. S.; Roth, B.; Sanfilippo, P. J. J. Am. Chem. Soc. 1982, 104, 1784.
(c) Kende, A. S.; Roth, B.; Sanfilippo, P. J.; Blacklock, T. J. J. Am. Chem. Soc. 1982, 104, 5808.
(d) Toyota, M.; Wada, T.; Fukumoto, K.; Ihara, M. J. Am. Chem. Soc. 1998, 120, 4916.
[9] Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978.
[10] Zhang, Z.; Liu, C.; Kinder, R. E.; Han, X.; Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2006, 128, 9066.
[11] (a) Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1983, 105, 3720.
(b) Stork, G.; Mook, R., Jr. J. Am. Chem. Soc. 1987, 109, 2829.
[12] (a) Trost, B. M.; Rise, F. J. Am. Chem. Soc. 1987, 109, 3161.
(b) Yamada, H.; Aoyagi, S.; Kibayashi, C. Tetrahedron Lett. 1997, 38, 3027.
(c) Oh, C. H.; Rhim, C. Y.; Kim, M.; Park, D. I.; Gupta, A. K. Synlett 2005, 2694.
(d) Oh, C. H.; Jung, H. H. Tetrahedron Lett. 1999, 40, 1535.
(e) Oh, C. H.; Jung, H. H.; Kim, J. S.; Cho, S. W. Angew. Chem., Int. Ed. 2000, 39, 752.
(f) Oh, C. H.; Han, J. W.; Kim, J. S.; Um, S. Y.; Jung, H. H.; Jang, W. H.; Won, H. S. Tetrahedron Lett. 2000, 41, 8365.
[13] For reviews on oxa-Micheal reactions, see:
(a) Nising, C. F.; Bräse, S. Chem. Soc. Rev. 2008, 37, 1218.
(b) Nising, C. F.; Bräse, S. Chem. Soc. Rev. 2012, 41, 988.
[14] (a) Hudlicky, T.; Natchus, M. G.; Sinai-Zingde, G. J. Org. Chem. 1987, 52, 4641.
(b) Hsu, D.-S.; Liao, C.-C. Org. Lett. 2003, 5, 4741.
[15] (a) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869.
(b) Tang, R.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 2100.
(c) Evans, D. A.; Andrews, G. C.; Sims, C. L. J. Am. Chem. Soc. 1971, 93, 4956.
(d) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
[16] For selected applications in total synthesis, see:
(a) Engstrom, K. M.; Mendoza, M. R.; Navarro-Villalobos, M.; Gin, D. Y. Angew. Chem., Int. Ed. 2001, 40, 1128.
(b) Taber, D. F.; Teng, D. J. Org. Chem. 2002, 67, 1607.
(c) Pelc, M. J.; Zakarian, A. Org. Lett. 2005, 7, 1629.
(d) Lu, C.-D.; Zakarian, A. Angew. Chem., Int. Ed. 2008, 47, 6829.
(e) Ilardi, E. A.; Isaacman, M. J.; Qin, Y.-C.; Shelly, S. A.; Zakarian, A. Tetrahedron 2009, 65, 3261.
[17] (a) Riley, H. L.; Morley, J. F.; Friend, N. A. C. J. Chem. Soc. 1932, 1875.
(b) Waitkins, G. R.; Clark, C. W. Chem. Rev. 1945, 36, 235.
(c) Fürstner, A.; Gastner, T. Org. Lett. 2000, 2, 2467.
[18] Blay, G.; Cardona, L.; García, B.; Pedro, J. R. J. Org. Chem. 1993, 58, 7204.
[19] (a) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A. J. Chem. Soc., Perkin Trans. 1 1998, 355.
(b) Furlan, R. L. E.; Mata, E. G.; Mascaretti, O. A.; Pena, C.; Coba, M. P. Tetrahedron 1998, 54, 13023.
(c) Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378.
/
| 〈 |
|
〉 |
