The anislactone type sesquiterpenoids, (-)-merrilactones A-C and anislactones A-B, contain[5-5] bicyclic carbocyclic skeleton, two γ-butyrolactone structural units, featuring congested stereocenters and a high oxidation level. This type of natural products shows potent neurotrophic activity. Particularly, (-)-merrilactone A exhibits excellent neurotrophic activity even at lower concentration with potential for treating neurodisease such as Elzheimer disease. Due to their complex caged structures and excellent biologic profiles, the synthesis of aislactone-type sesquiterpenoids has attracted considerable attention from synthetic communities. This article summarizes the recent advances in the synthesis of this type of sesquiterpenoids.
Li Jian
,
He Long
,
Zhou Zhiqiang
,
Zhen Yanxia
,
Xie Weiqing
. Advances in the Synthesis of Anislactone-Type Sesquiterpenes[J]. Chinese Journal of Organic Chemistry, 2020
, 40(10)
: 3166
-3176
.
DOI: 10.6023/cjoc202005028
[1] Xiong, Y.-Z.; Gong, Z. L. China Condiment. 2008, 9, 28(in Chinese). (熊燕子, 龚正礼, 中国调味品, 2008, 9, 28.)
[2] Kouno, I.; Mori, K.; Kawano, N.; Sato, S. Tetrahedron Lett. 1989, 30, 7451.
[3] Huang, J.; Yokoyama, R.; Yang, C.; Fukuyama, Y. Tetrahedron Lett. 2000, 41, 6111.
[4] Huang, J.; Yang, C.; Masami T.; Fukuyama, Y. Tetrahedron Lett. 2001, 57, 4691.
[5] Liu, J.-F.; Wang, Y.-F.; Bi, Y.-P.; Li, H.-J.; Jia, L.; Bi, Y.-F.; Zhang, Y.-B. Tetrahedron Lett. 2013, 54, 4834.
[6] Birman, V. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 2080.
[7] Meng, Z.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2005, 44, 1511.
[8] Inoue, M.; Sato, T.; Hirama, M. J. Am. Chem. Soc. 2003, 125, 10772.
[9] Inoue, M.; Sato, T.; Hirama, M. Angew. Chem. Int. Ed. 2006, 45, 4843.
[10] Inoue, M.; Lee, N.; Kasuya, S.; Sato, T.; Hirama, M.; Moriyama, M.; Fukuyama, Y. J. Org. Chem. 2007, 72, 3065.
[11] Mehta, G.; Singh, S. R. Tetrahedron Lett. 2005, 46, 2079.
[12] Mehta, G.; Singh, S. R. Angew. Chem. Int. Ed. 2006, 45, 953.
[13] (a) He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2007, 129, 498.
(b) He, W.; Huang, J.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2008, 130, 300.
[14] Iriondo-Alberdi, J.; Perea-Buceta, J. E.; Greaney, M. F. Org. Lett. 2005, 7, 3969.
[15] (a) Shi, L.; Meyer, K.; Greaney, M. F. Angew. Chem. Int. Ed. 2010, 49, 9250.
(b) Nazef, N.; Davies, R. D. M.; Greaney, M. F. Org. Lett. 2012, 14, 3720.
[16] Chen, J.; Gao, P.; Yu, F.; Yang, Y.; Zhu, S.; Zhai, H. Angew. Chem. Int. Ed. 2012, 51, 5897.
[17] Liu, W.; Wang, B. Chem. Eur. J. 2018, 24, 16511.
