An alternative total synthesis of bolivianine
- Corresponding author: Bo Liu, chembliu@scu.edu.cn
Citation: Jin-Peng Li, Chang-Chun Yuan, Biao Du, Bo Liu. An alternative total synthesis of bolivianine[J]. Chinese Chemical Letters, ;2017, 28(1): 113-116. doi: 10.1016/j.cclet.2016.06.013
Acebey L., Sauvain M., Beck S.. Bolivianine, a new sesterpene with an unusual skeleton from Hedyosmum angustifolium, and its isomer, isobolivianine[J]. Org. Lett., 2007,9:4693-4696. doi: 10.1021/ol7015725
Yuan C., Du B., Yang L., Liu B.. Bioinspired total synthesis of bolivianine:a DielsAlder/intramolecular hetero-Diels-Alder cascade approach[J]. J. Am. Chem. Soc., 2013,135:9291-9294. doi: 10.1021/ja4040335
Yang Y., Li J., Du B.. An entry to vinylcyclopropane through palladiumcatalyzed intramolecular cyclopropanation of alkenes with unstabilized allylic tosylhydrazones[J]. Chem. Commun., 2015,51:6179-6182. doi: 10.1039/C5CC00235D
Du B., Yuan C., Yu T.. Asymmetric total synthesis of onoseriolide, bolivianine, and isobolivianine[J]. Chem. Eur. J., 2014,20:2613-2622. doi: 10.1002/chem.v20.9
(a) S.K.S. Amoah, F.L. Oliveira, M.W. Biavatti, et al., Sesquiterpene lactones from the leaves of Hedyosmum brasiliense (Chloranthaceae), Phytochemistry 87(2013) 126-132;
(b) L. Acebey, V. Jullian, M. Sauvain, et al., Anti-Leishmanial Lindenane Sesquiterpenes from Hedyosmum angustifolium, Planta Med. 76(2010) 365-368;
(c) A.P. Trentin, A.R.S. Santos, J.B. Calixto, Antinociception caused by the extract of Hedyosmum brasiliense and its active principle, the Sesquiterpene Lactone 13-Hydroxy-8, 9-dehydroshizukanolide, Planta Med. 65(1999) 517-521;
(d) F. Bohlmann, C. Zdero, H. Robinson, et al., Onoseriolid, ein neues sesquiterpenlacton aus Onoseris albicans, Phytochemistry 19(1980) 689-691.
Cong H., Becker C.F., Elliott S.J.. Silver nanoparticle-catalyzed Diels-Alder cycloadditions of 2'-hydroxychalcones[J]. J. Am. Chem. Soc., 2010,132:7514-7518. doi: 10.1021/ja102482b
Armstrong A., Critchley T.J., Mortlock A.A.. Synthesis studies on CP-225, 917 and CP-263, 114:concise synthesis of the bicycle core using an intramolecular Mukaiyama aldol reaction[J]. J. Chem. Soc. Perkin Trans., 2002,1:1344-1350.
(a) A.K. Chakraborti, L. Sharma, R. Gulhane, et al., Electrostatic catalysis by ionic aggregates:scope and limitations of Mg (ClO4)2 as acylation catalyst, Tetrahedron 59(2003) 7661-7668;
(b) A.K. Chakraborti, R. Gulhane, Indium (Ⅲ) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, and amines, Tetrahedron Lett. 44(2003) 6749-6753;
(c) M.S. Niasari, T. Khosousi, S. Hydarzadeh, Highly selective esterification of tertbutanol by acetic acid anhydride over alumina-supported InCl3, GaCl3, FeCl3, ZnCl2, CuCl2, NiCl2, CoCl2 and MnCl2 catalysts, J. Mol. Catal. A:Chem. 235(2005) 150-153.
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