Total syntheses of bupleurynol and its analog
- Corresponding author: Ma Kai-Qing, makaiqing@sxu.edu.cn
Citation: Ma Kai-Qing, Miao Yan-Hong, Gao Xiao-Xia, Chao Jian-Bin, Zhang Xiang, Qin Xue-Mei. Total syntheses of bupleurynol and its analog[J]. Chinese Chemical Letters, ;2017, 28(5): 1035-1038. doi: 10.1016/j.cclet.2016.11.032
R. Negri, Polyacetylenes from terrestrial plants and fungi: recent phytochemical and biological advances, Fitoterapia 106(2015) 92-109.
Heydenreuter W., Kunold E., Sieber S.A.. Alkynol natural products target ALDH2 in cancer cells by irreversible binding to the active site[J]. Chem. Commun., 2015,51:15784-15787. doi: 10.1039/C5CC06424D
Matsuura H., Saxena G., Farmer S.. Antibacterial and antifungal polyine compounds from Glehnia littoralis ssp. leiocarpa[J]. Planta Med., 1996,62:256-259. doi: 10.1055/s-2006-957872
Liang L.F., Wang T., Cai Y.S.. Brominated polyunsaturated lipids from the Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors[J]. Eur. J. Med. Chem., 2014,79:290-297. doi: 10.1016/j.ejmech.2014.04.003
Kim H., Chin J., Choi H.. Phosphoiodyns A and B, unique phosphoruscontaining iodinated polyacetylenes from a Korean sponge Placospongia sp[J]. Org. Lett., 2012,15:100-103.
Chou T.C., Dong H., Zhang X.. Multifaceted cytoprotection by synthetic polyacetylenes inspired by the ginseng-derived natural product panaxytriol[J]. Proc. Natl. Acad. Sci. U. S. A., 2011,108:14336-14341. doi: 10.1073/pnas.1111332108
Zhang B., Wang Y., Yang S.P.. Ivorenolide A, an unprecedented immunosuppressive macrolide from Khaya ivorensis:structural elucidation and bioinspired total synthesis[J]. J. Am. Chem. Soc., 2012,134:20605-20608. doi: 10.1021/ja310482z
Wang Y., Liu Q.F., Xue J.J.. Ivorenolide B, an immunosuppressive 17-membered macrolide from Khaya ivorensis:structural determination and total synthesis[J]. Org. Lett., 2014,16:2062-2065. doi: 10.1021/ol500667d
Dong H., He L., Huang M.. Anti-inflammatory components isolated from Atractylodes macrocephala Koidz[J]. Nat. Prod. Res., 2008,22:1418-1427. doi: 10.1080/14786410801931629
Zhou Z.F., Menna M., Cai Y.S.. Polyacetylenes of marine origin:chemistry and bioactivity[J]. Chem. Rev., 2015,115:1543-1596. doi: 10.1021/cr4006507
Shi Shun A.L.. Tykwinski, Synthesis of naturally occurring polyynes[J]. Angew. Chem. Int. Ed., 2006,45:1034-1057. doi: 10.1002/(ISSN)1521-3773
Zhao J., Guo Y.Z., Meng X.S.. The toxic principles of Bupleurum longiradiatum[J]. Acta Pharm. Sin., 1987,22:507-511.
Huang H.Q., Zhang X., Shen Y.H.. Polyacetylenes from Bupleurum longiradiatum[J]. J. Nat. Prod., 2009,72:2153-2157. doi: 10.1021/np900534v
Liu J., Fang Y., Yang L.. A qualitative and quantitative determination and pharmacokinetic study of four polyacetylenes from Radix Bupleuri by UPLCPDA-MS[J]. J. Pharm. Biomed. Anal., 2015,111:257-265. doi: 10.1016/j.jpba.2015.04.002
Antunes L.M., Organ M.G.. Metal-catalyzed coupling reactions on an olefin template:the total synthesis of bupleurynol[J]. Tetrahedron Lett., 2003,44:6805-6808. doi: 10.1016/S0040-4039(03)01753-2
Ghasemi H., Antunes L.M., Organ M.G.. Use of olefin templates in queued chemical transformations using late transition metal catalysis. Total synthesis of cis and trans bupleurynol via a single multireaction sequence[J]. Org. Lett., 2004,6:2913-2916. doi: 10.1021/ol0489853
Sindhu K.S., Thankachan A.P., Sajitha P.S.. Recent developments and applications of the Cadiot-Chodkiewicz reaction[J]. Org. Biomol. Chem., 2015,13:6891-6905. doi: 10.1039/C5OB00697J
Ma S., Lu X., Li Z.. A novel regio-and stereospecific hydrohalogenation reaction of 2-propynoic acid and its derivatives[J]. J. Org. Chem., 1992,57:709-713. doi: 10.1021/jo00028a055
Jiang X.Y., Xu X.H., Qing F.L.. Design and concise synthesis of gemdifluoromethylenated analogue of 7-epi-castanospermine[J]. Chin. Chem. Lett., 2014,25:1115-1120. doi: 10.1016/j.cclet.2014.04.018
Wan M., Yao M., Gong J.Y.. Synthesis of the tetracyclic core of chlorospermines[J]. Chin. Chem. Lett., 2015,26:272-276. doi: 10.1016/j.cclet.2015.01.037
Bellina F., Carpita A., Mannocci L.. First total synthesis of naturally occurring (-)-nitidon and its enantiomer[J]. Eur. J. Org. Chem., 2004,12:2610-2619.
Corey E.J., Fuchs P.L.. A synthetic method for formyl→ethynyl conversion (RCHO→RCCH or RC=CR')[J]. Tetrahedron Lett., 1972,13:3769-3772. doi: 10.1016/S0040-4039(01)94157-7
Kiliçkiran P., Hopf H., Dix I.. Preparation of highly hindered polyenynes[J]. Eur. J. Org. Chem., 2010,21:4035-4045.
Carreras J., Gopakumar G., Gu L.. Polycationic ligands in gold catalysis:synthesis and applications of extremely p-acidic catalysts[J]. J. Am. Chem. Soc., 2013,135:18815-18823. doi: 10.1021/ja411146x
Galler D.J., Parker K.A.. Five easy pieces. The total synthesis of phosphoiodyn A (and placotylene A)[J]. Org. Lett., 2015,17:5544-5546. doi: 10.1021/acs.orglett.5b02642
Dess D., Martin J.. Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones[J]. J. Org. Chem., 1983,48:4155-4156. doi: 10.1021/jo00170a070
Chen D.L., Wang F.P., Liu X.Y.. A convergent approach to the tetracyclic core of atisane diterpenes[J]. Chin. Chem. Lett., 2016,27:59-62. doi: 10.1016/j.cclet.2015.09.005
Ma K., Liao D., Yang S.. Studies towards the synthesis of the functionalized C3-C14 decalin framework of alchivemycin A[J]. Org. Chem. Front., 2016,3:251-258. doi: 10.1039/C5QO00343A
Zhang Z., Lu C., Liu X.. Global and targeted metabolomics reveal that bupleurotoxin, a toxic type of polyacetylene, induces cerebral lesion by inhibiting GABA receptor in mice[J]. J. Proteome Res., 2013,13:925-933.
Schmidt B., Audorsch S.. Stereoselective total synthesis of atractylodemayne A, a conjugated 2(E), 8(Z), 10(E)-triene-4, 6-diyne[J]. Org. Lett., 20016,18:1162-1165.
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