The total synthesis of (±)-arisugacin A

Tetrahedron

Volumn 59, Issue 3, 2003, Pages 311-324

  Hsung, Richard P ^a   Cole, Kevin P ^a   Zehnder, Luke R ^a   Wang, Jiashi ^a   Wei, Lin Li ^a   Yang, Xiao Fang ^a   Coverdale, Heather A ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Arisugacin A; Formal 3+3 cycloaddition; Iminium salts; Retro aldol aldol sequence; Stereoselective pericyclic ring closure

Indexed keywords

1 OXATRIENE; ALKENE DERIVATIVE; ARISUGACIN A; CHOLINESTERASE INHIBITOR; PYRONE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DIHYDROXYLATION; DRUG SYNTHESIS; ELECTRON; OXYGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 0037434033     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01524-7     Document Type: Article

References (59)

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16. (a) For preliminary communications on the formal [3+3] cycloaddition approach, see: (a) Shen, H. C.; Degen, S. J.; Mulder, J. A.; Hsung, R. P.; Douglas C. J.; Golding, G. M.; Johnson, E. W.; Mathias, D. S.; Morgan, C. D.; Mueller, K. L.; Shih, R. A., Abstract No. ORGN-664, 216th ACS National Meeting, Boston, MA, Fall, 1998. (b) Hsung R.P., Shen H.C., Douglas C.J., Morgan C.D., Degen S.J., Yao L.J. J. Org. Chem. 64:1999;690.
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22. For related studies, see: (a) Cravotto G., Nano G.M., Tagliapietra S. Synthesis. 2001;49 (b) Hua D.H., Chen Y., Sin H.-S., Robinson P.D., Meyers C.Y., Perchellet E.M., Perchellet J.-P., Chiang P.K., Biellmann J.-P. Acta Crystallogr. C55:1999;1698 (c) Krasnaya Z.A., Bogdanov V.S., Burova S.A., Smirnova Y.V. Russ. Chem. 44:1995;2118 (d) Heber D., Berghaus T. J. Heterocycl. Chem. 31:1994;1353 (e) Appendino G., Cravotto G., Tagliapietra S., Nano G.M., Palmisano G. Helv. Chim. Acta. 73:1990;1865 (f) Schuda P.F., Price W.A. J. Org. Chem. 52:1987;1972 (g) de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 21:1984;85. see also 1369.
23. For related studies, see: (a) Cravotto G., Nano G.M., Tagliapietra S. Synthesis. 2001;49 (b) Hua D.H., Chen Y., Sin H.-S., Robinson P.D., Meyers C.Y., Perchellet E.M., Perchellet J.-P., Chiang P.K., Biellmann J.-P. Acta Crystallogr. C55:1999;1698 (c) Krasnaya Z.A., Bogdanov V.S., Burova S.A., Smirnova Y.V. Russ. Chem. 44:1995;2118 (d) Heber D., Berghaus T. J. Heterocycl. Chem. 31:1994;1353 (e) Appendino G., Cravotto G., Tagliapietra S., Nano G.M., Palmisano G. Helv. Chim. Acta. 73:1990;1865 (f) Schuda P.F., Price W.A. J. Org. Chem. 52:1987;1972 (g) de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 21:1984;85. see also 1369.
24. For related studies, see: (a) Cravotto G., Nano G.M., Tagliapietra S. Synthesis. 2001;49 (b) Hua D.H., Chen Y., Sin H.-S., Robinson P.D., Meyers C.Y., Perchellet E.M., Perchellet J.-P., Chiang P.K., Biellmann J.-P. Acta Crystallogr. C55:1999;1698 (c) Krasnaya Z.A., Bogdanov V.S., Burova S.A., Smirnova Y.V. Russ. Chem. 44:1995;2118 (d) Heber D., Berghaus T. J. Heterocycl. Chem. 31:1994;1353 (e) Appendino G., Cravotto G., Tagliapietra S., Nano G.M., Palmisano G. Helv. Chim. Acta. 73:1990;1865 (f) Schuda P.F., Price W.A. J. Org. Chem. 52:1987;1972 (g) de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 21:1984;85. see also 1369.
25. For related studies, see: (a) Cravotto G., Nano G.M., Tagliapietra S. Synthesis. 2001;49 (b) Hua D.H., Chen Y., Sin H.-S., Robinson P.D., Meyers C.Y., Perchellet E.M., Perchellet J.-P., Chiang P.K., Biellmann J.-P. Acta Crystallogr. C55:1999;1698 (c) Krasnaya Z.A., Bogdanov V.S., Burova S.A., Smirnova Y.V. Russ. Chem. 44:1995;2118 (d) Heber D., Berghaus T. J. Heterocycl. Chem. 31:1994;1353 (e) Appendino G., Cravotto G., Tagliapietra S., Nano G.M., Palmisano G. Helv. Chim. Acta. 73:1990;1865 (f) Schuda P.F., Price W.A. J. Org. Chem. 52:1987;1972 (g) de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 21:1984;85. see also 1369.
26. For related studies, see: (a) Cravotto G., Nano G.M., Tagliapietra S. Synthesis. 2001;49 (b) Hua D.H., Chen Y., Sin H.-S., Robinson P.D., Meyers C.Y., Perchellet E.M., Perchellet J.-P., Chiang P.K., Biellmann J.-P. Acta Crystallogr. C55:1999;1698 (c) Krasnaya Z.A., Bogdanov V.S., Burova S.A., Smirnova Y.V. Russ. Chem. 44:1995;2118 (d) Heber D., Berghaus T. J. Heterocycl. Chem. 31:1994;1353 (e) Appendino G., Cravotto G., Tagliapietra S., Nano G.M., Palmisano G. Helv. Chim. Acta. 73:1990;1865 (f) Schuda P.F., Price W.A. J. Org. Chem. 52:1987;1972 (g) de March P., Moreno-Mañas M., Casado J., Pleixats R., Roca J.L., Trius A. J. Heterocycl. Chem. 21:1984;85. see also 1369.
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36. For aza-variant of this formal [3+3] cycloaddition reaction using vinylogous amides, see: (a) Sklenicka H.M., Hsung R.P., McLaughlin M.J., Wei L.-L., Gerasyuto A.I., Brennessel W.W. J. Am. Chem. Soc. 124:2002;10435 (b) Wei L.-L., Sklenicka H.M., Gerasyuto A.I., Hsung R.P. Angew. Chem. Int. Ed. 40:2001;1516 (c) Sklenicka H.M., Hsung R.P., Wei L.-L., McLaughlin M.J., Gerasyuto A.I., Degen S.J., Mulder J.A. Org. Lett. 2:2000;1161 (d) Hsung R.P., Wei L.-L., Sklenicka H.M., Douglas C.J., McLaughlin M.J., Mulder J.A., Yao L. J. Org. Lett. 1:1999;509.
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41. For Õmura's approach, see: (a) Handa M., Sunazuka T., Nagai K., Kimura R., Shirahata T., Tian Z.M., Otoguro K., Harigaya Y., Õmura S. J. Antibiotics. 54:2001;382. For their total synthesis of (±)-arisugacin A, see: (b) Sunazuka T., Handa M., Nagai K., Shirahata T., Harigaya Y. Org. Lett. 4:2002;367.
42. For our total synthesis, see: (a) Wang J., Cole K.P., Wei L.L., Zehnder L.R., Hsung R.P. Tetrahedron Lett. 43:2002;3337 (b) Cole K.P., Hsung R.P., Yang X.-F. Tetrahedron Lett. 43:2002;3341.
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57. When using various peroxyacids, the best result gave the tentatively assigned hexacycle (Ref. 28) as the major product in 28% yield with the desired product in only 21% yield unlike those reported (Ref. 16).
58. The hexacycle was likely a result of intramolecular trapping of the incipient oxocarbenium intermediate by the C1-OH. Such facile trapping by oxygen nucleophiles agrees well with our previous experience in the model studies and with the hexacycle that at this point is not useful for the arisugacin synthesis.
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