Abstract
Several new 2-substituted allyl bromides were synthesized through cyclopropanol intermediates and were then involved in the Barbier allylation of (R)-2,3-O-isopropylideneglyceraldehyde in the presence of zinc in a mixture of tetrahydrofuran and saturated aqueous ammonium chloride to obtain the corresponding homoallylic alcohols with high diastereoselectivity. The possibility of using the latter as building blocks for macrocyclic antitumor agents (laulimalides) and their synthetic analogs was demonstrated.
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Yamamoto, Y. and Asao, N., Chem. Rev., 1993, vol. 93, p. 2207. doi https://doi.org/10.1021/cr00022a010
Li, C.-J., Tetrahedron, 1996, vol. 52, p. 5643. doi https://doi.org/10.1016/0040-4020(95)01056-4
Yus, M., Gonzalez-Gomez, J.C., and Foubelo, F., Chem. Rev., 2011, vol. 111, p. 7774. doi https://doi.org/10.1021/cr1004474
Venkatesham, A. and Nagaiah, K., Tetrahedron: Asymmetry, 2012, vol. 23, p. 1186. doi https://doi.org/10.1016/j.tetasy.2012.07.015
Kageyama, M., Miyagi, T., Yoshida, M., Nagasawa, T., Ohrui, H., and Kuwahara, S., Biosci. Biotechnol. Biochem., 2012, vol. 76, p. 1219. doi https://doi.org/10.1271/bbb.120134
Yadav, J., Reddy, N.M., Rahman, M.A., and Prasad Reddy, B.VS., Tetrahedron, 2013, vol. 69, p. 8618. doi https://doi.org/10.1016/j.tet.2013.07.072
Sanyal, I., Shukla, B., Barman, P.D., and Banerjee, A.K., Tetrahedron Lett., 2013, vol. 54, p. 2637. doi https://doi.org/10.1016/j.tetlet.2013.03.035
Zimmermann, N., Pinard, P., Carboni, B., Gosselin, P., Gaulon-Nourry, C., Dujardin, G., Collet, S., Lebreton, J., and Mathe-Allainmat, M., Eur. J. Org. Chem., 2013, p. 2303. doi https://doi.org/10.1002/ejoc.201201728
Holt, D. and Gaunt, M.J., Angew. Chem., Int. Ed., 2015, vol. 54, p. 7857. doi https://doi.org/10.1002/anie.201501995
Heathcock, C.H., Young, S.D., Hagen, J.P., Pirrung, M.C., White, C.T., and VanDerveer, D., J. Org. Chem., 1980, vol. 45, p. 3846. doi https://doi.org/10.1021/jo01307a023
Hafner, A., Duthaler, R.O., Marti, R., Rihs, G., Rothe-Streit, P., and Schwarzenbach, F., J. Am. Chem. Soc., 1992, vol. 114, p. 2321. doi https://doi.org/10.1021/ja00033a005
Solomon, M.S. and Hopkins, P.B., J. Org. Chem., 1993, vol. 58, p. 2232. doi https://doi.org/10.1021/jo00060a045
Pan, C.-F., Zhang, Z.-H., Sun, G.-J., and Wang, Z.-Y., Org. Lett., 2004, vol. 6, p. 3059. doi https://doi.org/10.1021/ol049008u
Solomon, M.S. and Hopkins, P.B., Tetrahedron Lett., 1991, vol. 32, p. 3297. doi https://doi.org/10.1016/S0040-4039(00)92690-X
Liu, B. and Zhou, W.-S., Org. Lett., 2004, vol. 6, p. 71. doi https://doi.org/10.1021/ol036058a
Cheung, C.-M., Craig, D., and Todd, R.S., Synlett, 2001, p. 1611. doi https://doi.org/10.1055/s-2001-17442
Cossy, J., Willis, C., Bellosta, V., and Bouz, S., J. Org. Chem., 2002, vol. 67, p. 1982. doi https://doi.org/10.1021/jo010653d
Kiren, S. and Williams, L.J., Org. Lett., 2005, vol. 7, p. 2905. doi https://doi.org/10.1021/ol0508375
Nakashima, K., Kikuchi, N., Shirayama, D., Miki, T., Ando, K., Sono, M., Suzuki, S., Kawase, M., Kondoh, M., Sato, M., and Tori, M., Bull. Chem. Soc. Jpn., 2007, vol. 80, p. 387. doi https://doi.org/10.1246/bcsj.80.387
Xie, J., Ma, Y., and Horne, D.A., J. Org. Chem., 2011, vol. 76, p. 6169. doi https://doi.org/10.1021/jo200899v
Arthuis, M., Beaud, R., Gandon, V., and Roulland, E., Angew. Chem., Int. Ed., 2012, vol. 51, p. 1 510. doi https://doi.org/10.1002/anie.201205479
Li, M., Xiong, J., Huang, Y., Wang, L.-J., Tang, Y., Yang, G.-X., Liu, X.-H., Wei, B.-G., Fan, H., Zhao, Y., Zhai, W.-Z., and Hu, J.-F., Tetrahedron, 2015, vol. 71, p. 5285. doi https://doi.org/10.1016/j.tet.2015.06.020
Binder, W.H., Prenner, R.H., and Schmid, W., Tetrahedron, 1994, vol. 50, p. 749. doi https://doi.org/10.1016/S0040-4020(01)80790-0
Paquette, L.A. and Mitzel, T.M., Tetrahedron Lett., 1995, vol. 36, p. 6863. doi https://doi.org/10.1016/0040-4039(95)01439-O
Paquette, L.A. and Mitzel, T.M., J. Am. Chem. Soc., 1996, vol. 118, p. 1931. doi https://doi.org/10.1021/ja953682c
Chng, S.-S., Xu, J., and Loh, T.-P., Tetrahedron Lett., 2003, vol. 44, p. 4997. doi https://doi.org/10.1016/S0040-4039(03)01173-0
Moral, J.A., Moon, S.-J., Rodriguez-Torres, S., and Minehan, T.G., Org. Lett., 2009, vol. 11, p. 3734. doi https://doi.org/10.1021/ol901353f
Schmoelzer, C., Fischer, M., and Schmid, W., Eur. J. Org. Chem., 2010, p. 4886. doi https://doi.org/10.1002/ejoc.201000623
Mulzer, J. and Angermann, A., Tetrahedron Lett., 1983, vol. 24, p. 2843. doi https://doi.org/10.1016/S0040-4039(00)88039-9
Boucley, C., Cahiez, G., Carini, S., Cere, V., Comes-Franchini, M., Knochel, P., Pollicino, S., and Ricci, A., J. Organomet. Chem., 2001, vol. 624, p. 223. doi https://doi.org/10.1016/S0022-328X(00)00902-5
Bied, C., Collin, J., and Kagan, H.B., Tetrahedron, 1992, vol. 48, p. 3877. doi https://doi.org/10.1016/S0040-4020(01)88468-4
Alcaide, B., Almendros, P., Carrascosa, R., and Torres, M.R., Adv. Synth. Catal., 2010, vol. 352, p. 1277. doi https://doi.org/10.1002/adsc.201000124
Alcaide, B., Almendros, P., and Carrascosa, R., Tetrahedron, 2012, vol. 68, p. 9391. doi https://doi.org/10.1016/j.tet.2012.09.030
Sanyal, I., Barman, P.D., and Banerjee, A.K., Tetrahedron Lett., 2015, vol. 56, p. 789. doi https://doi.org/10.1016/j.tetlet.2014.12.065
Chen, Q., Qiu, X.-L., and Qing, F.-L., J. Org. Chem., 2006, vol. 71, p. 3762. doi https://doi.org/10.1021/jo0601157
Yue, X., Wu, Y.-Y., and Qing, F.-L., Tetrahedron, 2007, vol. 63, p. 1560. doi https://doi.org/10.1016/j.tet.2006.12.014
Xu, X.-H., You, Z.-W., Zhang, X., and Qing, F.-L., J. Fluorine Chem., 2007, vol. 128, p. 535. doi https://doi.org/10.1016/j.jfluchem.2007.01.007
Chen, Z.-H., Wang, R.-W., and Qing, F.-L., Tetrahedron Lett., 2012, vol. 53, p. 2171. doi https://doi.org/10.1016/j.tetlet.2012.02.062
Csuk, R. and Schroeder, C., J. Carbohydr. Chem., 1999, vol. 18, p. 285. doi https://doi.org/10.1080/07328309908543996
Bhalay, G., Clough, S., McLaren, L., Sutherland, A., and Willis, C.L., J. Chem. Soc., Perkin Trans. 1, 2000, p. 901. doi https://doi.org/10.1039/B200358A
Kameda, Y. and Nagano, H., Tetrahedron, 2006, vol. 62, p. 9751. doi https://doi.org/10.1016/j.tet.2006.07.054
Moral, J.A., Moon, S.-J., Rodriguez-Torres, S., and Minehan, T.G., Org. Lett., 2009, vol. 11, p. 3734. doi https://doi.org/10.1021/ol901353f
Dhanjee, H. and Minehan, T.G., Tetrahedron Lett., 2010, vol. 51, p. 5609. doi https://doi.org/10.1016/j.tetlet.2010.08.064
Kozyrkov, Yu.Yu. and Kulinkovich, O.G., Synlett, 2002, p. 443. doi https://doi.org/10.1055/s-2002-20461
Haym, I. and Brimble, M.A., Org. Biomol. Chem., 2012, vol. 10, p. 7649. doi https://doi.org/10.1039/C2OB26082D
Mineeva, I.V., Russ. J. Org. Chem., 2017, vol. 53, p. 433. doi https://doi.org/10.1134/S1070428017030204
Mineeva, I.V. and Kulinkovich, O.G., Russ. J. Org. Chem., 2008, vol. 44, p. 1261. doi https://doi.org/10.1134/S1070428008090029
Mineyeva, I.V. and Kulinkovich, O.G., Tetrahedron Lett., 2010, vol. 51, p. 1836. doi https://doi.org/10.1016/j.tetlet.2010.01.120
Mineeva, I.V., Russ. J. Org. Chem., 2014, vol. 50, p. 398. doi https://doi.org/10.1134/S1070428014030178
Mineeva, I.V., Russ. J. Org. Chem., 2016, vol. 52, p. 355. doi https://doi.org/10.1134/S1070428016030118
Mülzer, J. and Öhler, E., Chem. Rev., 2003, vol. 103, p. 3753. doi https://doi.org/10.1021/cr940368c
Trost, B.M., Amans, D., Seganish, W.M., and Chung, C.K., Chem. Eur. J., 2012, vol. 18, p. 2961. doi https://doi.org/10.1002/chem.201102899
Mineeva, I.V., Russ. J. Org. Chem., 2015, vol. 51, p. 920. doi https://doi.org/10.1134/S1070428015070052
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Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 4, pp. 635–644.
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Mineyeva, I.V. Functionalized 2-Substituted Allyl Bromides in the Barbier Allylation of (R)-2,3-O-Isopropylideneglyceraldehyde. Synthesis of the C8–C17, C8–C18, and C5–C17 Building Blocks of Laulimalides and Their Synthetic Analogs. Russ J Org Chem 55, 530–539 (2019). https://doi.org/10.1134/S1070428019040195
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DOI: https://doi.org/10.1134/S1070428019040195