Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

10.1002/anie.201107204

10.1126/science.aaa9349

aLavaud, C.; Massiot, G.InProgress in the Chemistry of Organic Natural Products;Kinghorn, A. D.; Falk, H.; Gibbons, S.; Kobayashi, J., Eds.Springer International Publishing AG:Switzerland, 2017; Vol.105, pp89–136.

bCordell, G. A.InChemistry of Heterocyclic Compounds: Indoles, Part Four, The Monoterpenoid Indole Alkaloids;Saxton, J. E., Ed.John Wiley & Sons, Inc.:Hoboken, NJ, 1983; Vol.25, pp467–537.

aLounasmaa, M.; Tolvanen, A.InThe Alkaloids: Chemistry and Pharmacology;Cordell, G. A., Ed.Academic Press, Inc.:San Diego, 1992; Vol.42, pp1–116.

bDopke, W.InThe Alkaloids: Chemistry and Physiology;Manske, R. H. F.; Rodrigo, R. G. A., Eds.Academic Press, Inc.:New York, 1981; Vol.20, 297–332.

Kam, T. S.; Lim, K. H.InThe Alkaloids: Chemistry and Biology;Cordell, G. A., Ed.Academic Press:The Netherlands, 2008; Vol.66, pp1–111.

10.1135/cccc19672523

Trojánek J., 1965, Chem. Ind., 28, 1261

10.1039/p29730002001

10.1016/0031-9422(93)85305-B

10.1016/S0031-9422(00)98283-9

10.1016/0031-9422(92)83674-N

10.1016/S0031-9422(97)00513-X

10.1016/S0031-9422(98)00492-0

10.1016/S0040-4039(97)00152-4

10.1002/anie.201602374

10.1021/np900576b

10.1021/ol9016172

10.1016/j.phytochem.2010.05.015

10.1021/np400214y

10.1021/np500289t

10.1039/c39740000164

10.1021/acs.jnatprod.5b00992

10.1016/S0031-9422(96)00496-7

10.1016/j.tet.2014.10.002

10.1016/S0031-9422(98)00721-3

10.1021/np50037a024

10.1016/j.phytochem.2014.09.014

10.1039/b512615k

10.3390/molecules13081875

10.1021/ja01023a065

10.1021/ja00730a046

10.1021/ja00860a023

10.1021/ja01085a029

aTan, P. S.Alkaloids from Malaysian Kopsia species. M.Sc. Dissertation,Chemistry Department, University of Malaya,Malaysia, 1993.

bSim, K. M.Alkaloids from Holarrhena, Kopsia and Tabernaemontana: Chemistry and Bioactivity. Ph.D. Thesis,Chemistry Department, University of Malaya,Malaysia, 2001.

10.1021/jo01044a011

10.1016/S0040-4020(01)85802-6

10.3987/COM-12-12511

10.1107/S0108767383001762

10.1107/S0021889800007184

10.1002/chir.20473

Spartan’14;Wavefunction, Inc:Irvine, CA, 2014.

Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.Gaussian 09, revision C.01;Gaussian Inc.:Wallingford, CT, 2010.

Bruhn, T.; Schaumlöffel, A.; Hemberger, Y.SpecDis, Version 1.64;University of Wuerzburg:Germany, 2015.