Ring expansion approach for the synthesis of the (3S,4S)-hexahydroazepine core of balanol and ophiocordin

Tetrahedron

Volumn 59, Issue 51, 2003, Pages 10325-10329

  Yadav, J S ^a   Srinivas, Ch ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Balanol; Ophiocordin; Ring expansion

Indexed keywords

BALANOL; GLUCONIC ACID; HETEROCYCLIC COMPOUND; HEXAMETHYLENEIMINE DERIVATIVE; PROTEIN KINASE C INHIBITOR; TRI O ACETYL DEXTRO GLUCAL; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; WITTIG REACTION;

EID: 0345357971     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.089     Document Type: Article

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24. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
25. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
26. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
27. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
28. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
29. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
30. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
31. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
32. For the synthesis and study of balanol analogues, see: (a) Heerding J.M., Lampe J.W., Darges J.W., Stamper M.L. Bioorg. Med. Chem. Lett. 5:1995;1839 (b) Jagdmann G.E. Jr., Defauw J.M., Lai Y.S., Crane H.M., Hall E.S., Buben J.A., Hu H., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2015 (c) Lai Y.S., Stamper M. Bioorg. Med. Chem. Lett. 5:1995;2147 (d) Lai Y.S., Menaldino D.S., Nichols J.B., Jagdmann G.E. Jr., Mylott F., Gillespie J., Hall S.E. Bioorg. Med. Chem. Lett. 5:1995;2151 (e) Lai Y.S., Mendoza J.S., Hubbard F., Kalter K. Bioorg. Med. Chem. Lett. 5:1995;2155 (f) Mendoza J.S., Jagdmann G.E. Jr., Gosnell P.A. Bioorg. Med. Chem. Lett. 5:1995;2211 (g) Hu H., Hollinshead S.P., Hall S.E., Kalter K., Ballas L.M. Bioorg. Med. Chem. Lett. 6:1996;973 (h) Jagdmann G.E. Jr., Defauw J.M., Lampe J.W., Darges J.W., Kalter K. Bioorg. Med. Chem. Lett. 6:1996;1759 (i) Crane H.M., Menaldino D.S., Jagdmann G.E. Jr., Darges J.W., Buben J.A. Bioorg. Med. Chem. Lett. 5:1996;2133 (j) Nielsen J., Lyngso L.O. Tetrahedron Lett. 37:1996;8439 (k) Defauw J.M., Murphy M.M., Jagdmann G.E. Jr., Hu H., Lampe J.W., Hollinshead S.P., Mitchell T.J., Crane H.M., Heerding J.M., Mendoza J.S., Davis J.E., Darges J.W., Hubbard F.R., Hall S.E. J. Med. Chem. 39: 1996;521 (l) Lai Y.S., Mendoza J.S., Jagdmann G.E. Jr., Menaldino D.S., Biggers C., Heerding J.M., Wilson J.W., Hall S.E., Jiang J.B., Janzen W.P., Ballas L.M. J. Med. Chem. 40:1997;226 (m) Koide K., Bunnage M.E., Paloma L.G., Kanter J.R., Taylor S.S., Brunton L.L., Nicolaou K.C. Chem. Biol. 2:1995;601.
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