Rapid construction of the unique BCD ring system of tricyclo[6.2.1.0] undecane in the C19-diterpenoid alkaloid aconitine
- Corresponding author: Xu Liang, liangxu@scu.edu.cn Wang Jian-Li, wangjianli0804@163.com
Citation:
Yang Xue, Cheng Bin, Cheng Hang, Xu Liang, Wang Jian-Li. Rapid construction of the unique BCD ring system of tricyclo[6.2.1.0] undecane in the C19-diterpenoid alkaloid aconitine[J]. Chinese Chemical Letters,
;2017, 28(8): 1788-1792.
doi:
10.1016/j.cclet.2017.03.032
F. P. Wang, Q. H. Chen, in: G. A. Cordell (Ed. ), In the Alkaloids: Chemistry and Biology, 69, Elsevier Science, Amsterdam, 2010, pp. 1-577.
Ameri A.. The effects of aconitum alkaloids on the central nervous system[J]. Prog. Neurobiol., 1998,56:211-235. doi: 10.1016/S0301-0082(98)00037-9
Goodall K.J., Barker D., Brimble M.A.. A review of advances in the synthesis of analogues of the delphinium-alkaloid methyllycaconitine[J]. Synlett, 2005:1809-1827.
(a) K. Wiesner, T. Y. R. Tsai, K. Huber, et al. , Total synthesis of talatisamine, a delphinine type alkaloid, J. Am. Chem. Soc. 96(1974) 4990-4992;
(b) K. Wiesner, T. Y. R. Tsai, K. P. Nambiar, A new stereospecific total synthesis of chasmanine and 13-desoxydelphonine, Can. J. Chem. 56(1978) 1451-1454;
(c) K. Wiesner, Total synthesis of delphinine-type alkaloids by simple, fourth generation methods, Pure Appl. Chem. 51(1979) 689-703.
Shi Y., Wilmot J.T., Nordstrom L.U.. Total synthesis, relay synthesis, and structural confirmation of the C18-norditerpenoid alkaloid neofinaconitine[J]. J. Am. Chem. Soc., 2013,135:14313-14320. doi: 10.1021/ja4064958
Marth C.J., Gallego G.M., Lee J.C.. Network-analysis-guided synthesis of weisaconitine D and liljestrandinine[J]. Nature, 2015,528:493-498. doi: 10.1038/nature16440
Nishiyama Y., Yokoshima S., Fukuyama T.. Total synthesis of (-)-cardiopetaline[J]. Org. Lett., 2016,18:2359-2362. doi: 10.1021/acs.orglett.6b00789
(a) J. L. van der Baan, J. W. F. K. Barnick, G. van Beek, et al. , Total synthesis of C19-diterpene alkaloids: construction of a functionalized ABCD-ring system, Tetrahedron 48(1992) 2773-2784;
(b) L. C. Baillie, J. R. Bearder, W. S. Li, et al. , Studies into the synthesis of a sub-unit of the neurotoxic alkaloid methyllycaconitine, J. Chem. Soc. Perkin Trans. 1(1998) 4047-4055;
(c) D. F. Taber, J. L. Liang, B. Chen, et al. , A model study toward the total synthesis of N-deacetyllappaconitine, J. Org. Chem. 70(2005) 8739-8742;
(d) G. A. Kraus, S. Kesavan, Preparation of advanced intermediates for the synthesis of both methyllycaconitine and racemulsonine via a common intermediate, Tetrahedron Lett. 46(2005) 1111-1113;
(e) R. M. Conrad, J. Du Bois, C-H amination in synthesis: an approach to the assembly of the B/C/D ring system of aconitine, Org. Lett. 9(2007) 5465-5468;
(f) K. Hagiwara, T. Tabuchi, D. Urabea, et al. , Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process, Chem. Sci. 7(2016) 4372-4378;
(g) T. Tabuchi, D. Urabe, M. Inoue, Construction of the fused pentacycle of talatisamine via a combination of radical and cationic cyclizations, J. Org. Chem. 81(2016) 10204-10213.
(a) Z. G. Liu, L. Xu, Q. H. Chen, et al. , Construction of A/E/F ring systems of C19-diterpenoid alkaloids with both C-1 and C-6 oxygen functions, Tetrahedron 68(2012) 159-165;
(b) H. Cheng, L. Xu, D. L. Chen, et al. , Construction of functionalized B/C/D ring system of C19-diterpenoid alkaloids via intramolecular Diels-Alder reaction followed by Wagnere-Meerwein rearrangement, Tetrahedron 68(2012) 1171-1176;
(c) Z. G. Liu, H. Cheng, M. J. Ge, et al. , PIDA-promoted intramolecular transannular aziridination to synthesize bridged azatricyclic amines related to methyllycaconitine, Tetrahedron 69(2013) 5431-5437;
(d) R. H. Mei, Z. G. Liu, H. Cheng, et al. , Synthesis of the 10-azatricyclo[3. 3. 2. 04, 8]decan core of C20-diterpenoid alkaloid racemulsonine via iodine(Ⅲ) promoted transannular aziridination reaction, Org. Lett. 15(2013) 2206-2209;
(e) H. Cheng, F. H. Zeng, D. Ma, et al. , Expedient construction of the ABEF azatetracyclic ring systems of lycoctonine-type and 7, 17-seco-type C19-diterpenoid alkaloids, Org. Lett. 16(2014) 2299-2301;
(f) M. L. Jiang, Y. J. Meng, W. Y. Xiong, et al. , Construction of functionalized ABEF ring system of C20-diterpenoid alkaloid racemulosine, Tetrahedron Lett. 57(2016) 1610-1612;
(g) Y. L. Li, M. C. Liu, Y. J. Meng, Two new entries to the ABF tricyclic ring system of 7, 17-seco-type C19-diterpenoid alkaloids via free radical cyclization and[3+2] cycloaddition of nitrile oxide, Tetrahedron 72(2016) 3171-3176.
(a)J. Marco-Contelles, B. Sánchez, Stereoelectronic effects in the 6-exo free radical cyclization of acyclic sugar derivatives: synthesis of branched chain cyclitols, J. Org. Chem. 58(1993) 4293-4297;
(b) D. Batty, D. Crich, S. M. Fortt, Synthesis of a 1a, 25-dihydroxyvitamin D3A ring model by an acyl radical cyclization, J. Chem. Soc. Chem. Commun. (1989) 1366-1368;
(c) J. Quirante, C. Escolano, F. Diaba, et al. , Radical promoted cyclizations of trichloroacetamides with silyl enol ethers and enol acetates: the role of the hydride reagent[tris(trimethylsilyl)silane vs. tributylstannane], J. Chem. Soc. Perkin Trans. 1(1999) 1157-1162;
(d) D. J. Wardrop, W. Zhang, N-methoxy-N-acylnitrenium ions: Application to the formal synthesis of (±)-desmethylamino FR901483, Org. Lett. 3(2001) 2353-2356.
(a) M. H. Filippini, R. Faure, J. Rodriguez, One-pot base-promoted tandem michael addition-intramolecular aldolization. Stereoselective synthesis and reactivity of 2-hydroxybicyclo[3. 2. 1]octan-8-ones, J. Org. Chem. 60(1995) 6872-6882;
(b) H. Hagiwara, M. Fukushima, K. Kinugawa, et al. , First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B, Tetrahedron 67(2011) 4061-4068.
Petrier C., Luche J.L.. Allylzinc reagents additions in aqueous media[J]. J. Org. Chem., 1985,50:910-912. doi: 10.1021/jo00206a047
(a) Y. K. Chen, R. K. Peddinti, C. C. Liao, Diastereoselective intramolecular Diels-Alder reactions of masked o-benzoquinones: a short entry to highly functionalized tricyclic[m. 2. 2. 0] ring systems, Chem. Commun. (2001) 1340-1341;
(b) S. K. Chittimalla, H. Y. Shiao, C. C. Liao, Domino retro Diels-Alder/Diels-Alder reaction: anefficient protocolfor the synthesis of highlyfunctionalized bicyclo[2. 2. 2]octenones and bicyclo[2. 2. 2]octadienones, Org. Biomol. Chem. 4(2006) 2267-2277;
(c) H. Cheng, F. H. Zeng, X. Yang, et al. , Collective total syntheses of atisane-type diterpenes and atisine-type diterpenoid alkaloids: (±)-spiramilactone B, (±)-spiraminol, (±)-dihydroajaconine, and (±)-spiramines C and D, Angew. Chem. Int. Ed. 55(2016) 392-396.
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