메뉴 건너뛰기




Volumn , Issue 5, 2001, Pages 629-633

Solid-support synthesis of 1,2-diols and γ-lactones through addition of α-(benzoyloxy)crotylindium reagents to aldehydes

Author keywords

Diols; Lactones; Solid phase synthesis; (benzoyloxy) crotylindium; (benzoyloxy) crotylstannane

Indexed keywords

ALDEHYDE; ALPHA (BENZOYLOXY)CROTYLINDIUM; BROMATE; GAMMA LACTONE DERIVATIVE; INDIUM; REAGENT; TIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0035039186     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13367     Document Type: Article
Times cited : (17)

References (43)
  • 1
    • 33749100952 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1998) J. Chem. Soc., Perkin Trans. I , pp. 3293
    • Brown, R.C.D.1
  • 2
    • 0032542115 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1998) Tetrahedron , vol.54 , pp. 15385
    • Booth, S.1    Hermkens, P.H.H.2    Ottenheijm, H.C.J.3    Rees, D.C.4
  • 3
    • 0001655235 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1997) Drugs of the Future , vol.22 , pp. 1007
    • Blackburn, C.1    Albericio, F.2    Kates, S.A.3
  • 4
    • 0031001699 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1997) Tetrahedron , vol.53 , pp. 5643
    • Hermkens, P.H.H.1    Ottenheijm, H.C.J.2    Rees, D.C.3
  • 5
    • 0030477258 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2288
    • Balkenhohl, F.1    Von Dem Bussche-Hünnefeld, C.2    Lansky, A.3    Zechel, C.4
  • 6
    • 0029930278 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1996) Tetrahedron , vol.52 , pp. 4527
    • Hermkens, P.H.H.1    Ottenheijm, H.C.J.2    Rees, D.C.3
  • 7
    • 7044263277 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1996) Chem, Rev. , vol.96 , pp. 555
    • Thompson, L.A.1    Ellman, J.A.2
  • 8
    • 33748237769 scopus 로고    scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 17
    • Früchtel, J.S.1    Jung, G.2
  • 9
    • 0029065615 scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1995) Tetrahedron , vol.51 , pp. 8135
    • Terrett, N.K.1    Gardner, M.2    Gordon, D.W.3    Kobylecki, R.J.4    Steele, J.5
  • 10
    • 0028243847 scopus 로고
    • For reviews, see: Brown, R. C. D, J. Chem. Soc., Perkin Trans. I 1998, 3293. Booth, S.; Hermkens, P. H, H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1998, 54, 15385. Blackburn, C.; Albericio, F.; Kates, S. A, Drugs of the Future 1997, 22, 1007. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1997, 53, 5643. Balkenhohl, F.; Von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288. Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Tetrahedron 1996, 52, 4527. Thompson, L. A.; Ellman, J. A. Chem, Rev. 1996, 96, 555, Früchtel, J, S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17. Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1233.
    • (1994) J. Med. Chem. , vol.37 , pp. 1233
    • Gordon, E.M.1    Barrett, R.W.2    Dower, W.J.3    Fodor, S.P.A.4    Gallop, M.A.5
  • 17
    • 0343384976 scopus 로고    scopus 로고
    • note
    • 3) δ : 130.6 (d), 127.8 (m, polystyrene), 119.4 (d), 71.9 (d), 40.3 (m, polystyrene), 28.8 (t); 27.2 (t), 17.7 (q), 13.6 (q), 9.5 (t).
  • 18
    • 0342515382 scopus 로고    scopus 로고
    • note
    • The carboxylic polystyrene resin (1% DVB cross-linked) with a loading of 2 mmol/g was purchased from Advanced Chemtech.
  • 20
    • 0342515381 scopus 로고    scopus 로고
    • note
    • The principal drawback in the use of dicyclohexyl-carbodiimide (DCC) is the formation of the dichloromethane-insoluble dicyclohexylurea (DCU) during acylation. The EDCI urea is soluble in dichloromethane.
  • 22
    • 0342515380 scopus 로고    scopus 로고
    • note
    • 4 and the solvent was removed in vacuo. Purification of the crude material by flash chromatography (EtOAc/petroleum ether: 20/80) afforded 1,2-diols.
  • 23
    • 0342949519 scopus 로고    scopus 로고
    • note
    • 3): 204.1964, found: 204.1970.
  • 24
    • 0342515376 scopus 로고    scopus 로고
    • note
    • +, 0.07), 113 (7), 112 (6), 96 (8), 95 (100), 93 (5), 83 (8), 81 (6), 79 (3), 73 (4), 72 (70), 71 (16), 70 (4), 69 (10), 67 (16), 57 (16), 55 (16), 53 (6).
  • 25
    • 0343384975 scopus 로고
    • Pons, J.-M.; Santelli, M. J. Org. Chem. 1989, 54, 877. Schobert, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 855. Handa, Y.; Inanaga, J, Tetrahedron Lett. 1987, 28, 5717.
    • (1989) J. Org. Chem. , vol.54 , pp. 877
    • Pons, J.-M.1    Santelli, M.2
  • 26
    • 84990086015 scopus 로고
    • Pons, J.-M.; Santelli, M. J. Org. Chem. 1989, 54, 877. Schobert, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 855. Handa, Y.; Inanaga, J, Tetrahedron Lett. 1987, 28, 5717.
    • (1988) Angew. Chem., Int. Ed. Engl. , vol.27 , pp. 855
    • Schobert, R.1
  • 27
    • 0142205141 scopus 로고
    • Pons, J.-M.; Santelli, M. J. Org. Chem. 1989, 54, 877. Schobert, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 855. Handa, Y.; Inanaga, J, Tetrahedron Lett. 1987, 28, 5717.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5717
    • Handa, Y.1    Inanaga, J.2
  • 28
    • 0028852540 scopus 로고
    • Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345. Tanaka, S.; Yasuda, A.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1975, 97, 3252.
    • (1995) Tetrahedron , vol.51 , pp. 1345
    • Becker, H.1    Soler, M.A.2    Sharpless, K.B.3
  • 33
  • 38
    • 0342515374 scopus 로고    scopus 로고
    • note
    • 2 (5 mL) at r.t., were added successively molecular sieves (310 mg), NaOAc (9 mg, 0.12 mmol, 0.5 equiv.) and PCC (155 mg, 0.72 mmol, 3 equiv.). The mixture was stirred at r.t, for 6 h before filtration through silica gel (EtOAc/cyclohexane: 70/30). The solvent was then removed in vacuo to give lactones.
  • 43
    • 0343820659 scopus 로고    scopus 로고
    • note
    • +, 0.7), 236 (5), 195 (11), 194 (66), 142 (14), 110 (15), 99 (100), 97 (22), 96 (18), 95 (11), 83 (21), 82 (12), 71 (25), 70 (16), 69 (27), 68 (12), 57 (16), 56 (13), 55 (25).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.