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Volumn 59, Issue 45, 2003, Pages 8979-8987

1,3-Polyol arrays via the stereoselective rearrangement of vinyl acetals

Author keywords

Diastereoselection; Lewis acids; Polyols

Indexed keywords

KETONE DERIVATIVE; POLYOL; VINYL ACETATE;

EID: 0142155227     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.03.004     Document Type: Article
Times cited : (19)

References (33)
  • 2
    • 0032486344 scopus 로고    scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1375
    • Schneider, C.1
  • 3
    • 0141692401 scopus 로고    scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (2001) Top. Curr. Chem. , vol.216 , pp. 51
    • Sinz, C.J.1    Rychnovsky, S.D.2
  • 4
    • 0028909931 scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1995) Tetrahedron , vol.51 , pp. 5315
    • Mori, Y.1    Asai, M.2    Kawade, J.-I.3    Furukawa, H.4
  • 5
    • 0023740262 scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4672
    • Nicolaou, K.C.1    Daines, R.A.2    Uenishi, J.3    Li, W.S.4    Papahatjis, D.P.5    Chakraborty, T.K.6
  • 6
    • 0002736658 scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 9
    • Poss, C.S.1    Schreiber, S.L.2
  • 7
    • 0030928918 scopus 로고    scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2058
    • Rychnovsky, S.D.1    Khire, U.R.2    Yang, G.3
  • 8
    • 0001164834 scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1988) Tetrahedron Lett. , pp. 5419
    • Mori, Y.1    Kuhara, M.2    Takeuchi, A.3    Suzuki, M.4
  • 9
    • 0001637960 scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4383
    • Mori, Y.1    Suzuki, M.2
  • 10
    • 0033828571 scopus 로고    scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8587
    • Zacuto, M.J.1    Leighton, J.L.2
  • 11
    • 0037055017 scopus 로고    scopus 로고
    • For a review, see: (a) Schneider C. Angew. Chem., Int. Ed. 37:1998;1375 (b) Sinz C.J., Rychnovsky S.D. Top. Curr. Chem. 216:2001;51 (c) Mori Y., Asai M., Kawade J.-I., Furukawa H. Tetrahedron. 51:1995;5315 (d) Nicolaou K.C., Daines R.A., Uenishi J., Li W.S., Papahatjis D.P., Chakraborty T.K. J. Am. Chem. Soc. 110:1988;4672 (e) Poss C.S., Schreiber S.L. Acc. Chem. Res. 27:1994;9 (f) Rychnovsky S.D., Khire U.R., Yang G. J. Am. Chem. Soc. 119:1997;2058 (g) Mori Y., Kuhara M., Takeuchi A., Suzuki M. Tetrahedron Lett. 1988;5419 (h) Mori Y., Suzuki M. Tetrahedron Lett. 30:1989;4383 (i) Zacuto M.J., Leighton J.L. J. Am. Chem. Soc. 122:2000;8587 (j) Zacuto M.J., O'Malley S.J., Leighton J.L. J. Am. Chem. Soc. 124:2002;7890.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7890
    • Zacuto, M.J.1    O'Malley, S.J.2    Leighton, J.L.3
  • 25
    • 0032192298 scopus 로고    scopus 로고
    • See, for example: (a) Davies-Coleman M.T., Garson M. J. Nat. Prod. Rep. 15:1998;477 (b) Rohr J. Angew. Chem., Int. Ed. 39:2000;2847 (c) Omura S. Macrolide Antibiotics. 1984;Academic, New York.
    • (1998) J. Nat. Prod. Rep. , vol.15 , pp. 477
    • Davies-Coleman, M.T.1    Garson, M.2
  • 26
    • 0034682909 scopus 로고    scopus 로고
    • See, for example: (a) Davies-Coleman M.T., Garson M. J. Nat. Prod. Rep. 15:1998;477 (b) Rohr J. Angew. Chem., Int. Ed. 39:2000;2847 (c) Omura S. Macrolide Antibiotics. 1984;Academic, New York.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2847
    • Rohr, J.1
  • 27
    • 0032192298 scopus 로고    scopus 로고
    • See, for example: (a). New York: Academic
    • See, for example: (a) Davies-Coleman M.T., Garson M. J. Nat. Prod. Rep. 15:1998;477 (b) Rohr J. Angew. Chem., Int. Ed. 39:2000;2847 (c) Omura S. Macrolide Antibiotics. 1984;Academic, New York.
    • (1984) Macrolide Antibiotics
    • Omura, S.1
  • 28
    • 0035900460 scopus 로고    scopus 로고
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (2001) J. Org. Chem. , vol.66 , pp. 7825
    • Marshall, J.A.1    Schaaf, G.M.2
  • 29
    • 0032544464 scopus 로고    scopus 로고
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2354
    • Evans, D.A.1    Carter, P.A.2    Carreira, E.M.3    Prunet, J.A.4    Charette, A.B.5    Lautens, M.6
  • 30
    • 0033152931 scopus 로고    scopus 로고
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1652
    • Scheidt, K.A.1    Tasaka, A.2    Bannister, T.D.3    Wendt, M.D.4    Roush, W.R.5
  • 31
    • 0031906655 scopus 로고    scopus 로고
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 187
    • Guo, J.S.1    Duffy, K.J.2    Stevens, K.L.3    Dalko, P.I.4    Roth, R.M.5    Hayward, M.M.6    Kishi, Y.7
  • 32
    • 0032504072 scopus 로고    scopus 로고
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (1998) J. Org. Chem. , vol.63 , pp. 4572
    • Panek, J.S.1    Jain, N.F.2
  • 33
    • 0000719768 scopus 로고    scopus 로고
    • See, for example: (a)
    • See, for example: (a) Marshall J.A., Schaaf G.M. J. Org. Chem. 66:2001;7825 (b) Evans D.A., Carter P.A., Carreira E.M., Prunet J.A., Charette A.B., Lautens M. Angew. Chem., Int. Ed. 37:1998;2354 (c) Scheidt K.A., Tasaka A., Bannister T.D., Wendt M.D., Roush W.R. Angew. Chem., Int. Ed. 38:1999;1652 (d) Guo J.S., Duffy K.J., Stevens K.L., Dalko P.I., Roth R.M., Hayward M.M., Kishi Y. Angew. Chem., Int. Ed. 37:1998;187 (e) Panek J.S., Jain N.F. J. Org. Chem. 63:1998;4572 (f) BouzBouz S., Popkin M.E., Cossy J. Org. Lett. 2:2000;3449.
    • (2000) Org. Lett. , vol.2 , pp. 3449
    • BouzBouz, S.1    Popkin, M.E.2    Cossy, J.3


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