Total synthesis of (+)-ambruticin S

Tetrahedron

Volumn 59, Issue 35, 2003, Pages 6819-6832

  Berberich, Stephen M ^a   Cherney, Robert J ^a   Colucci, John ^a   Courillon, Christine ^a   Geraci, Leo S ^a   Kirkland, Thomas A ^a   Marx, Matthew A ^a   Schneider, Matthias F ^a   Martin, Stephen F ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

Carbohydrates; Enantioselective; Furan; Julia coupling; Oxygen heterocycles; Rearrangement; Ring closing metathesis

Indexed keywords

1 [(BENZOTHIAZOLO)SULFONYL]METHYL 2 METHYL 3 (TERT BUTYLDIMETHYLSILYLOXY)METHYLCYCLOPROPANE; 2 (1 PHENYLSULFONYL 2 METHYL 3 PENTEN 4 YL) 5 METHYL 6 ETHYL 3,6 DIHYDROPYRAN; ACETONE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AMBRUTICIN; CYCLOPROPANE DERIVATIVE; EPOXIDE; FURAN DERIVATIVE; LACTONE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG; [2,3 BIS O TERT BUTYLDIMETHYLSILYL 4,6 DIDEOXY 6 (METHOXYCARBONYL)DEXTRO GLUCO BETA C PYRANOSYL]ALDEHYDE;

ARTICLE; CYCLOPROPANATION; DEPROTECTION REACTION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

DRYAS IULIA;

EID: 0041572913     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00370-3     Document Type: Article

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13. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
14. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
15. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
16. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
17. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
18. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
19. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
20. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
21. For selected synthetic studies toward ambruticin S, see: (a) Barnes N.J., Davidson A.H., Hughes L.R., Procter G. J. Chem. Soc., Chem. Commun. 1985;1292-1294 (b) Sinay P. Bioorganic Heterocycles 1986: Synthesis, Mechanism and Bioactivity. 1986;Elsevier, Amsterdam. pp 59-70 (c) Burke S.D., Armistead D.M., Schoenen F.J., Fevig J.M. Tetrahedron. 42:1986;2787-2801 (d) Proctor G., Russell A.T., Murphy P.J., Tan T.S., Mather A.N. Tetrahedron. 44:1988;3953-3973 (e) Davidson A.H., Eggleton N., Wallace I.H. J. Chem. Soc., Chem. Commun. 1991;378-380 (f) Markó I.E., Bayston D.J. Tetrahedron. 50:1994;7141-7156 (g) Nagasawa T., Handa Y., Onoguchi Y., Ohba S., Suzuki K. Synlett. 1995;739-741 (h) Liu L., Donaldson W.A. Synlett. 1996;103-104 (i) Markó I.E., Bayston D.J. Synthesis. 1996;297-304 (j) Wakamatsu H., Isono N., Mori M. J. Org. Chem. 62:1997;8917-8922 (k) Michelet V., Adiey K., Bulic B., Genêt J.-P., Dujardin G., Rossignol S., Brown E., Toupet L. Eur. J. Org. Chem. 64:1999;2885-2892.
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33. For example, see: (a) Martin S.F., Gluchowski C., Campbell C.L., Chapman R.C. J. Org. Chem. 49:1984;2512-2513 (b) Martin S.F., Guinn D.E. J. Org. Chem. 52:1987;5588-5593 (c) Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606 (d) Martin S.F., Dodge J.A., Burgess L.E., Limberakis C., Hartmann M. Tetrahedron. 52:1996;3229-3246 (e) Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., Mulhern T.A. J. Am. Chem. Soc. 116:1994;4674-4688 (f) Martin S.F., Hida T., Kym P.R., Loft M., Hodgson A. J. Am. Chem. Soc. 119:1997;3193-3194 (g) Martin S.F., Limberakis C., Burgess L.E., Hartmann M. Tetrahedron. 55:1999;3561-3572.
34. For example, see: (a) Martin S.F., Gluchowski C., Campbell C.L., Chapman R.C. J. Org. Chem. 49:1984;2512-2513 (b) Martin S.F., Guinn D.E. J. Org. Chem. 52:1987;5588-5593 (c) Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606 (d) Martin S.F., Dodge J.A., Burgess L.E., Limberakis C., Hartmann M. Tetrahedron. 52:1996;3229-3246 (e) Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., Mulhern T.A. J. Am. Chem. Soc. 116:1994;4674-4688 (f) Martin S.F., Hida T., Kym P.R., Loft M., Hodgson A. J. Am. Chem. Soc. 119:1997;3193-3194 (g) Martin S.F., Limberakis C., Burgess L.E., Hartmann M. Tetrahedron. 55:1999;3561-3572.
35. For example, see: (a) Martin S.F., Gluchowski C., Campbell C.L., Chapman R.C. J. Org. Chem. 49:1984;2512-2513 (b) Martin S.F., Guinn D.E. J. Org. Chem. 52:1987;5588-5593 (c) Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606 (d) Martin S.F., Dodge J.A., Burgess L.E., Limberakis C., Hartmann M. Tetrahedron. 52:1996;3229-3246 (e) Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., Mulhern T.A. J. Am. Chem. Soc. 116:1994;4674-4688 (f) Martin S.F., Hida T., Kym P.R., Loft M., Hodgson A. J. Am. Chem. Soc. 119:1997;3193-3194 (g) Martin S.F., Limberakis C., Burgess L.E., Hartmann M. Tetrahedron. 55:1999;3561-3572.
36. For example, see: (a) Martin S.F., Gluchowski C., Campbell C.L., Chapman R.C. J. Org. Chem. 49:1984;2512-2513 (b) Martin S.F., Guinn D.E. J. Org. Chem. 52:1987;5588-5593 (c) Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606 (d) Martin S.F., Dodge J.A., Burgess L.E., Limberakis C., Hartmann M. Tetrahedron. 52:1996;3229-3246 (e) Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., Mulhern T.A. J. Am. Chem. Soc. 116:1994;4674-4688 (f) Martin S.F., Hida T., Kym P.R., Loft M., Hodgson A. J. Am. Chem. Soc. 119:1997;3193-3194 (g) Martin S.F., Limberakis C., Burgess L.E., Hartmann M. Tetrahedron. 55:1999;3561-3572.
37. For example, see: (a) Martin S.F., Gluchowski C., Campbell C.L., Chapman R.C. J. Org. Chem. 49:1984;2512-2513 (b) Martin S.F., Guinn D.E. J. Org. Chem. 52:1987;5588-5593 (c) Martin S.F., Zinke P.W. J. Org. Chem. 56:1991;6600-6606 (d) Martin S.F., Dodge J.A., Burgess L.E., Limberakis C., Hartmann M. Tetrahedron. 52:1996;3229-3246 (e) Martin S.F., Lee W.-C., Pacofsky G.J., Gist R.P., Mulhern T.A. J. Am. Chem. Soc. 116:1994;4674-4688 (f) Martin S.F., Hida T., Kym P.R., Loft M., Hodgson A. J. Am. Chem. Soc. 119:1997;3193-3194 (g) Martin S.F., Limberakis C., Burgess L.E., Hartmann M. Tetrahedron. 55:1999;3561-3572.
38. For reviews of RCM in synthesis, see: (a) Schuster M., Blechert S. Angew. Chem. Int. Ed. Engl. 36:1997;2037-2056 (b) Grubbs R.H., Chang S. Tetrahedron. 54:1998;4413-4450 (c) Wright D.L. Curr. Org. Chem. 3:1999;211-240 (d) Fürstner A. Angew. Chem. Int. Ed. 39:2000;3012-3043.
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