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(b) Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmwe, N. E.; Brankiewicz, A. J.; Steinman, C. E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601-1605.
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French, J.C.8
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For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
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Lewy, D.S.1
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Soenen, D.R.3
Boger, D.L.4
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0037075845
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For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
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McCluskey, A.1
Sim, A.T.R.2
Sakoff, J.A.3
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5
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0030820773
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For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
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De Jong, R.S.1
Mulder, N.H.2
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6
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0030977738
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Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748-1753.
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Boger, D.L.1
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Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161-4167.
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Boger, D.L.1
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8
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0035477040
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(a) Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667-3670.
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Chavez, D.E.1
Jacobsen, E.N.2
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10
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0037035352
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(c) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. Chem. Commun. 2002, 742-743.
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(2002)
Chem. Commun.
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Miyashita, K.1
Ikejiri, M.2
Kawasaki, H.3
Maemura, S.4
Imanishi, T.5
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13
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0035850265
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For synthetic studies of 1, see: (a) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235. (b) Kiyotsuka, Y.; Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2002, 43, 2725-2729.
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Org. Lett.
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Cossy, J.1
Pradaux, F.2
BouzBouz, S.3
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14
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0037041358
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For synthetic studies of 1, see: (a) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235. (b) Kiyotsuka, Y.; Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2002, 43, 2725-2729.
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Tetrahedron Lett.
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Kiyotsuka, Y.1
Igarashi, J.2
Kobayashi, Y.3
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15
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0141662619
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note
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Jacobsen, Imanishi, Hatakeyama, and Falck utilized Stille or Suzuki cross-coupling for the triene construction. Compound 2 is the common intermediate of Jacobsen, Imanishi, Hatakeyama, and Kobayashi.
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16
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0030883527
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Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738-8739.
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J. Am. Chem. Soc.
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Matsumura, K.1
Hashiguchi, S.2
Ikariya, T.3
Noyori, R.4
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17
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0141439732
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note
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Same strategy was employed in Jacobsen's synthesis.
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19
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0033526380
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Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178.
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Yoshikawa, N.1
Yamada, Y.M.A.2
Das, J.3
Sasai, H.4
Shibasaki, M.5
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20
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0030863510
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(b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871-1873.
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Angew. Chem., Int. Ed. Engl.
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Yamada, Y.M.A.1
Yoshikawa, N.2
Sasai, H.3
Shibasaki, M.4
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23
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0034596326
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(a) Hamashima, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 7412-7413.
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Hamashima, Y.1
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24
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0035931483
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(b) Hamashima, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2001, 42, 691-694.
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Tetrahedron Lett.
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Hamashima, Y.1
Kanai, M.2
Shibasaki, M.3
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25
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0141774515
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note
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See Supporting Information for details.
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26
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0019495843
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The absolute configuration of 10 was determined by conversion to the known triol: Partridge, J. J.; Shiuey, S.-J.; Chadha, N. K.; Baggiolini, E. G.; Blount, J. F.; Uskokovic J. Am. Chem. Soc. 1981, 103, 1253-1255.
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J. Am. Chem. Soc.
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Partridge, J.J.1
Shiuey, S.-J.2
Chadha, N.K.3
Baggiolini, E.G.4
Blount, J.F.5
Uskokovic6
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27
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33751386025
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Keck, G. E.; Krishnamurthy, D.; Grier, M. C. J. Org. Chem. 1993, 58, 6543-6544.
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J. Org. Chem.
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Keck, G.E.1
Krishnamurthy, D.2
Grier, M.C.3
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28
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0033576661
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Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Yamamoto, H. Angew. Chem., Int. Ed. 1999, 38, 3701-3703.
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Angew. Chem., Int. Ed.
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Yanagisawa, A.1
Kageyama, H.2
Nakatsuka, Y.3
Asakawa, K.4
Matsumoto, Y.5
Yamamoto, H.6
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29
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0141662617
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note
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13C NMR with Imanishi's NMR chart. The stereoselectivity matches that of Yamamoto's transition-state model. AgF-catalyzed reaction in the absence of the chiral ligand resulted in no reaction. Addition of allylmagnesium bromide gave a 1:1 diastereomixture.
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30
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0141662618
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note
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The aldol reaction using 7 as a donor proved to be difficult possibly due to a fast retro-aldol reaction. Using 2,2-dimethyl-3-phenylpropanal as a model substrate in a reaction with the lithium enolate derived from 7 gave the product in only 28%. The reaction did not proceed with the zinc enolate. LLB (10 mol %), however, promoted the reaction efficiently, and the product was obtained in 72% yield.
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31
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0141439731
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note
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Diastereoisomers could not be separated at this stage. The relative configuration of C-8 and C-9 was determined by NOE measurement on acetonide 22.
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32
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0141439730
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note
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2O and 72% ee with LLB.
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33
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0030788440
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For a beneficial effect of BINOL substitution on a catalytic asymmetric nitroaldol reaction, see: Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256.
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(1997)
Angew. Chem., Int. Ed. Engl.
, vol.36
, pp. 1236-1256
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Shibasaki, M.1
Sasai, H.2
Arai, T.3
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34
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0141439729
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note
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Other diastereomers ((9S, 11S)- and (9S, 11R)- derived from 18b) were separable at this stage (14 and 4%, respectively). The relative configuration of C-9 and C-11 was determined by NOE measurement. See Supporting Information for details.
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35
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84989539773
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Nishikawa, T.; Shibuya, S.; Hosokawa, S.; Isobe, M. Synlett 1994, 485-486.
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(1994)
Synlett
, pp. 485-486
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Nishikawa, T.1
Shibuya, S.2
Hosokawa, S.3
Isobe, M.4
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36
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84892620357
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Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507.
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(1997)
J. Org. Chem.
, vol.62
, pp. 7507
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Myers, A.G.1
Zheng, B.2
Movassaghi, M.3
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39
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0141551232
-
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note
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Absolute configuration of 24 was confirmed comparing the sign of the optical rotation to the reported data by Hatakeyama. Two steps (phosphate ester formation and deprotection) are necessary from 24 to 1.
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-
-
-
40
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0035840992
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Ligands 11L and 12L are commercially available from Junsei Chemical Co., Ltd. (fax: +81-3-3270-5461)
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Yabu, K.; Masumoto, S.; Yamasaki, S.; Hamashima, Y.; Kanai, M.; Du, W.; Curran, D. P.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9908-9909. Ligands 11L and 12L are commercially available from Junsei Chemical Co., Ltd. (fax: +81-3-3270-5461).
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(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9908-9909
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Yabu, K.1
Masumoto, S.2
Yamasaki, S.3
Hamashima, Y.4
Kanai, M.5
Du, W.6
Curran, D.P.7
Shibasaki, M.8
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