Chinese Journal of Organic Chemistry >
Recent Progresses in Total Synthesis of (+)-Biotin
Received date: 2012-03-04
Revised date: 2012-05-14
Online published: 2012-05-22
Supported by
Project supported by the Doctoral Scientific Foundation of Henan University of Traditional Chinese Medicine (No. BSJJ2010-28).
(+)-Biotin is one of the B vitamins. The study on total synthesis of (+)-biotin is an incessant pursuit since it was discovered half century ago. During the past ten years great advances in this field have been made. The synthetic approaches toward the target molecule can be classified into two series: the enatioselective syntheses and the stereospecific syntheses. In former approach, modification of the already existed Hoffmann-La-Roche’s lactone-thiolactone approach was further developed in diversified ways, especially the great advance in asymmetric synthesis of the chiral framework of (+)-biotin, which had been put into industrial practice successfully; in terms of the latter approach, L-cysteine or cystine can be regarded as more logical starting materials. Enriched by a plenty of ingenious novel strategies and tactics, this approach evolved more facile and practical than before.
Key words： (+)-biotin; total synthesis; progress
Zhong Zheng , Wu Xuefen , Chen Fener . Recent Progresses in Total Synthesis of (+)-Biotin[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1792 -1802 . DOI: 10.6023/cjoc1203041
[1] Uskokovic. M. R. Biotin in Encyclopedia of Chemical Technology, Vol. 24, Eds.: Kirk, R. E.; Othmer, D. E., Wiley, New York, 1984, p. 41.
[2] (a) Minko, T.; Paranjpe, P. V.; Qiu, B.; Lalloo, A.; Won, R.; Stein, S.; Sinko, P. J. Cancer Chemother. Pharmacol. 2002, 50, 143.
(b) Green, N. M. Biochem. J. 1963, 89, 585.
(c) Melamed, M. D.; Green, N. M. Biochem. J. 1963, 89, 591.
(d) Green, N. M. Adv. Protein Chem. 1975, 29, 85.
(e) Fuhr, J. P. Jr.; He, H.; Goldfarb, N.; Nash, D. B. Dis. Manage. 2005, 8, 265.
[3] De Clercq, P. J. Chem. Rev. 1997, 97, 1755.
[4] (a) Goldberg, M. W.; Sternbach, L. H. US 2489232, 1951 [Chem. Abstr. 1951, 45, 184].
(b) Goldberg, M. W.; Sternbach, L. H. US 2489235 1951 [Chem. Abstr. 1951, 45, 186a].
(c) Goldberg, M. W.; Sternbach, L. H. US 2489238 1951 [Chem. Abstr. 1951, 45, 186g].
[5] (a) Chen, F.-E.; Ling, X.-H.; Lu, Y.-X.; Zhang, X.-Y.; Peng, X.-H. Chem. J. Chin. Univ. 2001, 22, 1141 (in Chinese).
(陈芬儿, 凌秀红, 吕银祥, 张晓跃, 彭晓华, 高等化学学报, 2001, 22, 1141.)
(b) Chen, F.-E. CN 1443766, 2003 [Chem. Abstr. 2003, 143, 326351].
[6] Zhang, G.-J.; Chen, J.-H.; Wu, Z.-G.; Zhang, F.; Shen, R.-P. Chin. J. Pharm. 2009, 40, 168 (in Chinese).
(张国钧, 陈建辉, 吴志刚, 张符, 沈润溥, 中国医药工业杂志, 2009, 40, 168.)
[7] Matsuki, K.; Inoue, H.; Takeda, M. Tetrahedron Lett. 1993, 34, 1167.
[8] Chen, F.-E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004.
[9] Ostendorf, M.; Romagnoli, R.; Pereiro, J. C.; Roos, E. C.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron: Asymmetry 1997, 11, 1773.
[10] (a) Shimizu, M.; Nishigaki, Y.; Wakabayashi, A. Tetrahedron Lett. 1999, 40, 8873.
(b) Tamotsu, F.; Shimizu, M. JP 2000256360, 2000 [Chem. Abstr. 2000, 133, 237771].
[11] Chen, F.-E.; Dai, H.-F.; Kuang, Y.-Y.; Jia, H. Q. Tetrahedron: Asymmetry 2003, 14, 3667.
[12] Chen, F.-E.; Yuan, J.-L.; Dai, H.-F.; Kuang, Y.-Y.; Chu, Y. Synthesis 2003, 2155.
[13] Chen, F.-E.; Jia, H.-Q.; Chen, X.-X.; Dai, H.-F.; Xie, B.; Kuang, Y.-Y.; Zhao, J.-F. Chem. Pharm. Bull. 2005, 53, 743.
[14] Wehrli, C. WO 2004094367, 2004 [Chem. Abstr. 2004, 141, 395554].
[15] Schwarz, M.; Eckstein, J. WO 2001025215, 2001 [Chem. Abstr. 2001, 134, 281013].
[16] (a) Choi, C.; Tian, T.-S.; Deng, L. Synthesis 2001, 1737.
(b) Deng, L.; Liu, X.-F. WO 2004110609, 2004 [Chem. Abstr. 2004, 141, 363443].
[17] Florni, M.; Porcheddu, A.; Taddei, M. Tetrahedron Lett. 1999, 40, 4395.
[18] (a) Xiong, F.; Chen, X.-X.; Chen, F.-E. Tetrahedron: Asymmetry 2010, 21, 665.
(b) Xiong, F.; Chen, X.-X.; Liu, Z.-Q.; Chen, F.-E. Tetrahedron Lett. 2010, 51, 3670.
(c) Dai, H.-F.; Chen, X.-X.; Zhao, L.; Sheng, H.; Chen, F.-E. Adv. Synth. Catal. 2008, 350, 1635.
[19] Chen, F.-E. CN 1473832, 2004 [Chem. Abstr. 2004, 142, 373827].
[20] Chen, F.-E.; Jia, H.-Q.; Chen, X.-X.; Dai, H.-F.; Xie, B.; Kuang, Y.-Y.; Zhao, J.-F. Adv. Synth. Catal. 2005, 347, 549.
[21] Schwarz, M.; Heywang, U.; Kuppe, T. WO 2002004460, 2002 [Chem. Abstr. 2002, 136, 102234].
[22] Lu, Y.-X.; Huang, Y.-M.; Huang, Y.-F.; Lu, Y. Synth. Commun. 2002, 32, 781.
[23] (a) Yoshikawa, K.; Kurimoto, I.; Sakito, Y. JP 08217779, 1996 [Chem. Abstr. 1996, 125, 328709].
(b) Hirata, N.; Miyamoto, Y.; Takahashi, T. JP 10231298, 1998 [Chem. Abstr. 1998, 129, 216619].
(c) Yani, N.; Seko, S. JP 09263487, 1997 [Chem. Abstr. 1997, 127, 476676].
(d) Uemura, T.; Shirahta, M.; Miyamoto, Y. JP 11101235, 1999 [Chem. Abstr. 1999, 131, 264751].
[24] (a) Chen, F.-E.; Peng, X.-H.; Sun, G.-F. CN 1358725, 2002 [Chem. Abstr. 2002, 139, 381479].
(b) Lu, X.-Y. CN 1548440, 2004 [Chem. Abstr. 2004, 142, 772178].
[25] Koop, U.; Krummradt, H.; Schwarz, M.; Stoldt, J.; Eckstein, J.; Zehner, S.; Melichnar, W. DE 10001317, 2001 [Chem. Abstr. 2001, 135, 107188].
[26] Chen, F.-E.; Peng, Z.-Z.; Shao, L.-Y.; Cheng, Y. Acta Pharm. Sin. 1999, 34, 822 (in Chinese).
(陈芬儿, 彭作中, 邵兰英, 程煜, 药学学报, 1999, 34, 822.)
[27] Chen, F.-E.; Huang, Y.-D.; Fu, H.; Cheng, Y.; Zhang, D.-M.; Li, Y.-Y.; Peng, Z.-Z. Synthesis 2000, 2004.
[28] (a) Seki, M.; Shimizu, T. JP 2000191665, 2000 [Chem. Abstr. 2000, 133, 73893m].
(b) Seki, M.; Shimizu, T. Tetrahedron Lett. 2000, 41, 5099.
[29] (a) Kimura, M.; Seki, M. Tetrahedron Lett. 2005, 45, 1635;
(b) Mor, Y.; Seki, M. Synlett 2005, 2233.
[30] Chen, F.-E.; Fu, H.; Meng, G.; Luo, Y. F.; Yan, M. G. Chem. J. Chin. Univ. 2002, 23, 1060 (in Chinese).
(陈芬儿, 傅晗, 孟歌, 罗有富, 鄢明国, 高等学校化学学报, 2002, 23, 1060.)
[31] (a) Takahshi, T.; Myamoto, Y.; Mizuno, M.; Hirata, N.; Mizuno, T. JP 07330776, 1995 [Chem. Abstr. 1995, 124, 875668].
(b) Takahshi, T.; Myamoto, Y.; Mizuno, M.; Hirata, N. US 5859260, 1996 [Chem. Abstr. 1996, 126, 576441].
(c) Lehmann, S.; Koppe, T. US 20040030150, 2004 [Chem. Abstr. 2004, 142, 266823].
[32] (a) Heywang, U.; Bollinger, H.; Müller, H. R. WO 9843979, 1998 [Chem. Abstr. 1998, 129, 275786].
(b) Kiyoshima, Y.; Miyamoto, Y. JP 10367060, 1998 [Chem. Abstr. 1998, 128, 441734].
(c) Lin, D.; Liu, D.; Lu, X. CN 1778803, 2006 [Chem. Abstr. 2006, 146, 358894].
[33] Meng, G.; He, Y.-P.; Chen, F.-E. Synth. Commun. 2003, 33, 2593.
[34] (a) Chen, F.-E. CN 1374312, 2002 [Chem. Abstr. 2002, 140, 181254].
(b) Deshpade, P. B.; Holkar, A. G.; Karale, S. N.; Jafri, W. S. WO 2004041430, 2004 [Chem. Abstr. 2004, 142, 773110].
[35] Brieden, W.; McGarrity, J. WO 9815557, 1998 [Chem. Abstr. 1998, 128, 308348].
[36] (a) Chavan, S. P.; Tejwani, R. B.; Ravindranathan, T. J. Org. Chem. 2001, 66, 6197.
(b) Ravindranathan, H.; Chavan, S. B.; Subhash, P.; Rajkumar, R. B. IN 178927, 1998 [Chem. Abstr. 1998, 140, 303667].
[37] (a) Seki, M.; Hatsuda, M.; Mori, Y.; Yamada, S. Tetrahedron Lett. 2002, 43, 3267.
(b) Seki, M.; Hatsuda, M.; Mori, Y.; Yamada, S. J. Org. Chem. 2002, 67, 5527.
[38] (a) Seki, M.; Kimura, M.; Hatsuda, M.; Yashida, S.; Shimizu, T. Tetrahedron Lett. 2003, 44, 8905.
(b) Seki, M.; Kimura, M.; Hatsuda, M.; Yashida, S.; Yamada, S.; Shimizu, T. Chem. Eur. J. 2004, 10, 6102.
(c) Seki, M.; Hatsuda, M.; Yashida, S.; Shimizu, T. Tetrahedron Lett. 2004, 45, 6579.
(d) Seki, M.; Kimura, M.; Hatsuda, M.; Yashida, S.; Shimizu, T. US 20050038260, 2005 [Chem. Abstr. 2005, 144, 465455].
(e) Seki, M. WO 2004089878, 2004 [Chem. Abstr. 2004, 141, 365968].
[39] Mori, Y.; Kimura, M.; Seki, M. Synthesis 2003, 2311.
[40] (a) Chavan, S. P.; Chittiboyina, A. G.; Ravindranathan, T.; Kamat, S. K.; Kalkote, U. R. J. Org. Chem. 2005, 70, 1901.
(b) Chavan, S. P.; Chittiboyina, A. G.; Amar, G.; Kamat, S. K.; Kalkote, U. R.; Ravindranathan, T. EP 1219625, 2002 [Chem. Abstr. 2002, 137, 63120].
(c) Chen, K.-X.; Cheng, X.-W.; Jin, J.-M.; Sheng, L.-Q. Chin. J. Org. Chem. 2006, 26, 1309 (in Chinese).
(陈克喜, 程向炜, 金佳敏, 盛柳青, 有机化学, 2006, 26, 1309.)
[41] (a) Takahashi, M.; Sakurai, O.; Kokubo, O. S. H. JP 2001002679, 2001 [Chem. Abstr. 2001, 134, 100868].
(b) Zhao, J.; Li, Y. B.-Q.; Zhang, S. Fine Chem. 2004, 21, 30 (in Chinese).
(赵嘉, 李云政, 张青山, 精细化工, 2004, 21, 30.)
[42] Chavan, S. P.; Ramakrishna, G.; Gonnade, R. G.; Bhadbhade, M. M. Tetrahedron Lett. 2004, 45, 7307. Seki, M.; Shimizu, T.; Inubushi, K. Synthesis 2002, 361.
/
| 〈 |
|
〉 |
