Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: Application in the formal synthesis of macrosphelide A

Tetrahedron

Volumn 59, Issue 46, 2003, Pages 9127-9135

  Chakraborty, Tushar K ^a   Purkait, Subhas ^a   Das, Sanjib ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Epoxide opening; Epoxy alcohols; Macrosphelides; Sharpless epoxidation

Indexed keywords

ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; CARBOXYLIC ACID; MACROSPHELIDE A; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CHIRALITY; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS;

EID: 0142196126     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.070     Document Type: Article

References (38)

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21. (a) Yamada T., Iritani M., Minoura K., Numata A., Kobayashi Y., Wang Y.-G. J. Antibiot. 55:2002;147-154 (b) Yamada T., Iritani M., Doi M., Minoura K., Ito T., Numata A. J. Chem. Soc., Perkin Trans. 1. 2001;3046-3053 (c) Fukami A., Taniguchi Y., Nakamura T., Rho M.-C., Kawaguchi K., Hayashi M., Komiyama K., Omura S. J. Antibiot. 52:1999;501-504 (d) Numata A., Iritani M., Yamada T., Minoura K., Matsumura E., Yamori T., Tsuruo T. Tetrahedron Lett. 38:1997;8215-8218 (e) Takamatsu S., Hiraoka H., Kim Y.-P., Hayashi M., Natori M., Komiyama K., Omura S. J. Antibiot. 50:1997;878-880 (f) Takamatsu S., Kim Y.-P., Hayashi M., Hiraoka H., Natori M., Komiyama K., Omura S. J. Antibiot. 49:1996;95-98 (g) Hayashi M., Kim Y.-P., Hiraoka H., Natori M., Takamatsu S., Kawakubo T., Masuma R., Komiyama K., Omura S. J. Antibiot. 48:1995;1435-1439.
22. (a) Yamada T., Iritani M., Minoura K., Numata A., Kobayashi Y., Wang Y.-G. J. Antibiot. 55:2002;147-154 (b) Yamada T., Iritani M., Doi M., Minoura K., Ito T., Numata A. J. Chem. Soc., Perkin Trans. 1. 2001;3046-3053 (c) Fukami A., Taniguchi Y., Nakamura T., Rho M.-C., Kawaguchi K., Hayashi M., Komiyama K., Omura S. J. Antibiot. 52:1999;501-504 (d) Numata A., Iritani M., Yamada T., Minoura K., Matsumura E., Yamori T., Tsuruo T. Tetrahedron Lett. 38:1997;8215-8218 (e) Takamatsu S., Hiraoka H., Kim Y.-P., Hayashi M., Natori M., Komiyama K., Omura S. J. Antibiot. 50:1997;878-880 (f) Takamatsu S., Kim Y.-P., Hayashi M., Hiraoka H., Natori M., Komiyama K., Omura S. J. Antibiot. 49:1996;95-98 (g) Hayashi M., Kim Y.-P., Hiraoka H., Natori M., Takamatsu S., Kawakubo T., Masuma R., Komiyama K., Omura S. J. Antibiot. 48:1995;1435-1439.
23. (a) Yamada T., Iritani M., Minoura K., Numata A., Kobayashi Y., Wang Y.-G. J. Antibiot. 55:2002;147-154 (b) Yamada T., Iritani M., Doi M., Minoura K., Ito T., Numata A. J. Chem. Soc., Perkin Trans. 1. 2001;3046-3053 (c) Fukami A., Taniguchi Y., Nakamura T., Rho M.-C., Kawaguchi K., Hayashi M., Komiyama K., Omura S. J. Antibiot. 52:1999;501-504 (d) Numata A., Iritani M., Yamada T., Minoura K., Matsumura E., Yamori T., Tsuruo T. Tetrahedron Lett. 38:1997;8215-8218 (e) Takamatsu S., Hiraoka H., Kim Y.-P., Hayashi M., Natori M., Komiyama K., Omura S. J. Antibiot. 50:1997;878-880 (f) Takamatsu S., Kim Y.-P., Hayashi M., Hiraoka H., Natori M., Komiyama K., Omura S. J. Antibiot. 49:1996;95-98 (g) Hayashi M., Kim Y.-P., Hiraoka H., Natori M., Takamatsu S., Kawakubo T., Masuma R., Komiyama K., Omura S. J. Antibiot. 48:1995;1435-1439.
24. (a) Yamada T., Iritani M., Minoura K., Numata A., Kobayashi Y., Wang Y.-G. J. Antibiot. 55:2002;147-154 (b) Yamada T., Iritani M., Doi M., Minoura K., Ito T., Numata A. J. Chem. Soc., Perkin Trans. 1. 2001;3046-3053 (c) Fukami A., Taniguchi Y., Nakamura T., Rho M.-C., Kawaguchi K., Hayashi M., Komiyama K., Omura S. J. Antibiot. 52:1999;501-504 (d) Numata A., Iritani M., Yamada T., Minoura K., Matsumura E., Yamori T., Tsuruo T. Tetrahedron Lett. 38:1997;8215-8218 (e) Takamatsu S., Hiraoka H., Kim Y.-P., Hayashi M., Natori M., Komiyama K., Omura S. J. Antibiot. 50:1997;878-880 (f) Takamatsu S., Kim Y.-P., Hayashi M., Hiraoka H., Natori M., Komiyama K., Omura S. J. Antibiot. 49:1996;95-98 (g) Hayashi M., Kim Y.-P., Hiraoka H., Natori M., Takamatsu S., Kawakubo T., Masuma R., Komiyama K., Omura S. J. Antibiot. 48:1995;1435-1439.
25. (a) Yamada T., Iritani M., Minoura K., Numata A., Kobayashi Y., Wang Y.-G. J. Antibiot. 55:2002;147-154 (b) Yamada T., Iritani M., Doi M., Minoura K., Ito T., Numata A. J. Chem. Soc., Perkin Trans. 1. 2001;3046-3053 (c) Fukami A., Taniguchi Y., Nakamura T., Rho M.-C., Kawaguchi K., Hayashi M., Komiyama K., Omura S. J. Antibiot. 52:1999;501-504 (d) Numata A., Iritani M., Yamada T., Minoura K., Matsumura E., Yamori T., Tsuruo T. Tetrahedron Lett. 38:1997;8215-8218 (e) Takamatsu S., Hiraoka H., Kim Y.-P., Hayashi M., Natori M., Komiyama K., Omura S. J. Antibiot. 50:1997;878-880 (f) Takamatsu S., Kim Y.-P., Hayashi M., Hiraoka H., Natori M., Komiyama K., Omura S. J. Antibiot. 49:1996;95-98 (g) Hayashi M., Kim Y.-P., Hiraoka H., Natori M., Takamatsu S., Kawakubo T., Masuma R., Komiyama K., Omura S. J. Antibiot. 48:1995;1435-1439.
26. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
27. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
28. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
29. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
30. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
31. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
32. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
33. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
34. For earlier works on the syntheses of macrosphelides see: (a) Sharma G.V.M., Mouli C.C. Tetrahedron Lett. 43:2002;9159-9161 (b) Nakamura H., Ono M., Shida Y., Akita H. Tetrahedron: Asymmetry. 13:2002;705-713 (c) Nakamura H., Ono M., Makino M., Akita H. Heterocycles. 57:2002;327-336 (d) Kobayashi Y., Acharya H.P. Tetrahedron Lett. 42:2001;2817-2820 (e) Kobayashi Y., Kumar B.G., Kurachi T., Acharya H.P., Yamazaki T., Kitazume T. J. Org. Chem. 66:2001;2011-2018 (f) Ono M., Nakamura H., Konno F., Akita H. Tetrahedron: Asymmetry. 11:2000;2753-2764 (g) Kobayashi Y., Kumar B.G., Kurachi T. Tetrahedron Lett. 41:2000;1559-1563 (h) Kobayashi Y., Nakano M., Kumar G.B., Kishihara K. J. Org. Chem. 63:1998;7505-7515 (i) Sunazuka T., Hirose T., Harigaya Y., Takamatsu S., Hayashi M., Komiyama K., Omura S. J. Am. Chem. Soc. 119:1997;10247.
35. 1H NMR analysis of the Mosher ester.
36. Chakraborty T.K., Das S. Tetrahedron Lett. 42:2001;3387-3390.
37. Zacharie B., Gagnon L., Attardo G., Connolly T.P., St-Denis Y., Penney C.L. J. Med. Chem. 40:1997;2883-2894.
38. Awakura D.A., Fujiwara K., Murai A. Synlett. 2000;1733-1736.