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6444225900
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See refs 8-11 for a list of synthetic studies towards the spongistatins.
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Smith, A. B., III; Zhuang, L.; Brook, C. S.; Boldi, A. M.; McBriar, M. D.; Moser, W. H.; Murase, N.; Nakayama, K.; Verhoest, P. R.; Lin, Q. Tetrahedron Lett. 1997, 38, 8667.
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84987472577
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26
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6444233368
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note
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Prepared in two steps exploiting Evans oxazolidinone chemistry; see the Supporting Information.
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-
-
-
27
-
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6444239282
-
-
note
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Upon scale-up, TfOH (≃9 mol %) was added, as the reaction does not proceed otherwise, suggesting that adventitious water was more pronounced on small scale thereby generating TfOH in situ.
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-
-
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29
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6444222933
-
-
note
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The stereochemistry in (-)-11 was established on the basis of NOEs observed between the C(39), C(40), and C(43) hydrogens.
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30
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0026072975
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Davis, F. A.; Kumar, A.; Chen, B.-C. J. Org. Chem. 1991, 56, 1143.
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31
-
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6444238606
-
-
note
-
Silylation at C(42) served to minimize chelation-control in the reduction, which otherwise resulted in poor selectivity.
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-
-
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32
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6444227294
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Watanabe, Y.; Ogasawara, T.; Nakahira, H.; Matsuki, T.; Ozaki, S. Tetrahedron Lett. 1988, 29, 5359.
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Watanabe, Y.1
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26844522419
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35
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33947085552
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The C(38) stereochemistry was confirmed by Mosher ester analysis; see: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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Dale, J.A.1
Mosher, H.S.2
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36
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2142858450
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The C(38) stereochemistry was confirmed by Mosher ester analysis; see: Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092.
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84981895720
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Schreiber, J.; Maag, H.; Hashimoto, N.; Eschenmoser, A. Angew. Chem., Int. Ed. Engl. 1971, 10, 330.
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40
-
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6444228630
-
-
note
-
This is in the 1,5-syn sense, opposite to 1,5-anti stereoinduction observed for boron aldol reactions of simple β-alkoxy ketones, suggesting in this case, the overwhelming contribution from the more remote stereocenters; see ref 9.
-
-
-
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41
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0000275815
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2; see: (a) Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. (b) Evans, D. A.; Truesdale, L. K. J. Chem. Soc., Chem. Commun. 1973, 55.
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Maldonado, L.2
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42
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27144444200
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2; see: (a) Stork, G.; Maldonado, L. J. Am. Chem. Soc. 1971, 93, 5286. (b) Evans, D. A.; Truesdale, L. K. J. Chem. Soc., Chem. Commun. 1973, 55.
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Evans, D.A.1
Truesdale, L.K.2
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43
-
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6444226572
-
-
note
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See the Supporting Information for the preparation of 24.
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44
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0032541271
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Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986.
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Corey, E.J.1
Helal, C.J.2
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45
-
-
6444221368
-
-
note
-
The C(47) stereochemistry was confirmed by chemical correlation to an intermediate prepared in our previous synthesis.
-
-
-
-
46
-
-
0037035004
-
-
The synthesis of (-)-4 was previously disclosed; see: Smith, A. B., III; Doughty, V. A. D.; Sfouggatakis, C.; Bennett, C. S.; Koyanagi, J.; Takeuchi, M. Org. Lett. 2002, 4, 783.
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Smith III, A.B.1
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Sfouggatakis, C.3
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Koyanagi, J.5
Takeuchi, M.6
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47
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0001616071
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Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
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Inanaga, J.1
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Yamaguchi, M.5
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