메뉴 건너뛰기




Volumn 55, Issue 9, 1999, Pages 2639-2658

Synthesis and olfactory properties of regioisomeric alkynolides and (Z)- alkenolides

Author keywords

Hydroxy alkyne carboxylic acids; Cyclization; Macrolides; Odour and structure

Indexed keywords

MACROLIDE;

EID: 0033605408     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00041-1     Document Type: Article
Times cited : (11)

References (38)
  • 2
    • 0001779775 scopus 로고    scopus 로고
    • a) Kraft P, Cadalbert R. Synlett 1997:600-602. b) Note added in proof: For a recent review see Fráter G, Bajgrowicz JA, Kraft P. Tetrahedron 1998;54:7633-7703.
    • (1997) Synlett , pp. 600-602
    • Kraft, P.1    Cadalbert, R.2
  • 3
    • 0032474807 scopus 로고    scopus 로고
    • Note added in proof: For a recent review see
    • a) Kraft P, Cadalbert R. Synlett 1997:600-602. b) Note added in proof: For a recent review see Fráter G, Bajgrowicz JA, Kraft P. Tetrahedron 1998;54:7633-7703.
    • (1998) Tetrahedron , vol.54 , pp. 7633-7703
    • Fráter, G.1    Bajgrowicz, J.A.2    Kraft, P.3
  • 4
    • 0003072854 scopus 로고    scopus 로고
    • Review
    • a) Review: Kraft P, Tochtermann W. Synlett 1996:1029-1035. b) Rodefeld L, Heinemann I, Tochtermann W. Tetrahedron 1998;54:5265-5286.
    • (1996) Synlett , pp. 1029-1035
    • Kraft, P.1    Tochtermann, W.2
  • 7
    • 0025836376 scopus 로고    scopus 로고
    • a) Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991;32:5321-5324. b) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1995;36:5737-5740. c) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1996;37:8735-8738. d) Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see Fürstner A, Seidel G. Angew. Chem. 1998;110:1758-1760; Angew. Chem. Int. Ed. Engl. 1998;37:1734-1736.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 5321-5324
    • Boivin, J.1    Elkaim, L.2    Ferro, P.G.3    Zard, S.Z.4
  • 8
    • 0029088989 scopus 로고
    • a) Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991;32:5321-5324. b) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1995;36:5737-5740. c) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1996;37:8735-8738. d) Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see Fürstner A, Seidel G. Angew. Chem. 1998;110:1758-1760; Angew. Chem. Int. Ed. Engl. 1998;37:1734-1736.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 5737-5740
    • Boivin, J.1    Huppé, S.2    Zard, S.Z.3
  • 9
    • 0030602161 scopus 로고    scopus 로고
    • a) Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991;32:5321-5324. b) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1995;36:5737-5740. c) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1996;37:8735-8738. d) Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see Fürstner A, Seidel G. Angew. Chem. 1998;110:1758-1760; Angew. Chem. Int. Ed. Engl. 1998;37:1734-1736.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8735-8738
    • Boivin, J.1    Huppé, S.2    Zard, S.Z.3
  • 10
    • 0025836376 scopus 로고    scopus 로고
    • Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see
    • a) Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991;32:5321-5324. b) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1995;36:5737-5740. c) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1996;37:8735-8738. d) Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see Fürstner A, Seidel G. Angew. Chem. 1998;110:1758-1760; Angew. Chem. Int. Ed. Engl. 1998;37:1734-1736.
    • (1998) Angew. Chem. , vol.110 , pp. 1758-1760
    • Fürstner, A.1    Seidel, G.2
  • 11
    • 0038731101 scopus 로고    scopus 로고
    • a) Boivin J, Elkaim L, Ferro PG, Zard SZ. Tetrahedron Lett. 1991;32:5321-5324. b) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1995;36:5737-5740. c) Boivin J, Huppé S, Zard SZ. Tetrahedron Lett. 1996;37:8735-8738. d) Note added in proof: For a recent synthesis of alkynolides via ring closure metathesis see Fürstner A, Seidel G. Angew. Chem. 1998;110:1758-1760; Angew. Chem. Int. Ed. Engl. 1998;37:1734-1736.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1734-1736
  • 12
    • 0013579484 scopus 로고
    • a) Johnson DA. J. Am. Chem. Soc. 1953;75:3636-3637. b) Couffignal R, Moreau JL. J. Organomet. Chem. 1977;127:C65-C68.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 3636-3637
    • Johnson, D.A.1
  • 14
    • 0000968707 scopus 로고
    • a) Turner JA, Jacks WS. J. Org. Chem. 1989;54:4229-4231. b) Brocksom TJ, Petragnani N, Rodrigues R. J. Org. Chem. 1974;39:2114-2116.
    • (1989) J. Org. Chem. , vol.54 , pp. 4229-4231
    • Turner, J.A.1    Jacks, W.S.2
  • 17
    • 0028115352 scopus 로고
    • a) Paterne M, Dhal R, Brown E. Bull. Chem. Soc. Jpn. 1989;62:1321-1324. b) Brobst SW, Townsend AC. Can. J. Chem. 1994;72:200-207.
    • (1994) Can. J. Chem. , vol.72 , pp. 200-207
    • Brobst, S.W.1    Townsend, A.C.2
  • 19
    • 0000733886 scopus 로고
    • a) Höfle G, Steglich W, Vorbrüggen H. Angew. Chem. 1978;90:602-615; Angew. Chem. Int. Ed. Engl. 1978;17:569. b) Boden EP, Keck GE. J. Org. Chem. 1985;50:2394-2395.
    • (1978) Angew. Chem. , vol.90 , pp. 602-615
    • Höfle, G.1    Steglich, W.2    Vorbrüggen, H.3
  • 20
    • 0017998510 scopus 로고
    • a) Höfle G, Steglich W, Vorbrüggen H. Angew. Chem. 1978;90:602-615; Angew. Chem. Int. Ed. Engl. 1978;17:569. b) Boden EP, Keck GE. J. Org. Chem. 1985;50:2394-2395.
    • (1978) Angew. Chem. Int. Ed. Engl. , vol.17 , pp. 569
  • 21
    • 33845378280 scopus 로고
    • a) Höfle G, Steglich W, Vorbrüggen H. Angew. Chem. 1978;90:602-615; Angew. Chem. Int. Ed. Engl. 1978;17:569. b) Boden EP, Keck GE. J. Org. Chem. 1985;50:2394-2395.
    • (1985) J. Org. Chem. , vol.50 , pp. 2394-2395
    • Boden, E.P.1    Keck, G.E.2
  • 22
    • 0013608973 scopus 로고
    • For other methods leading to E/Z mixtures or to E-isomers see: a
    • For other methods leading to E/Z mixtures or to E-isomers see: a) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1977;99:3867-3868. b) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1980;102:4743-4763. c) Fürstner A, Langemann K. J. Org. Chem. 1996;61:3942-3943. d) Fürstner A, Langemann K. Synthesis 1997:792-803.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 3867-3868
    • Trost, B.M.1    Verhoeven, T.R.2
  • 23
    • 33847084947 scopus 로고
    • For other methods leading to E/Z mixtures or to E-isomers see: a) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1977;99:3867-3868. b) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1980;102:4743-4763. c) Fürstner A, Langemann K. J. Org. Chem. 1996;61:3942-3943. d) Fürstner A, Langemann K. Synthesis 1997:792-803.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4743-4763
    • Trost, B.M.1    Verhoeven, T.R.2
  • 24
    • 0038206375 scopus 로고    scopus 로고
    • For other methods leading to E/Z mixtures or to E-isomers see: a) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1977;99:3867-3868. b) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1980;102:4743-4763. c) Fürstner A, Langemann K. J. Org. Chem. 1996;61:3942-3943. d) Fürstner A, Langemann K. Synthesis 1997:792-803.
    • (1996) J. Org. Chem. , vol.61 , pp. 3942-3943
    • Fürstner, A.1    Langemann, K.2
  • 25
    • 0030857814 scopus 로고    scopus 로고
    • For other methods leading to E/Z mixtures or to E-isomers see: a) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1977;99:3867-3868. b) Trost BM, Verhoeven TR. J. Am. Chem. Soc. 1980;102:4743-4763. c) Fürstner A, Langemann K. J. Org. Chem. 1996;61:3942-3943. d) Fürstner A, Langemann K. Synthesis 1997:792-803.
    • (1997) Synthesis , pp. 792-803
    • Fürstner, A.1    Langemann, K.2
  • 27
    • 0013631930 scopus 로고
    • a) Bestmann HJ, Schubert R. Angew. Chem. 1983;95:810-811; Angew. Chem. Int.ed. Engl. 1983;22:780-782. b) Bestmann HJ, Schubert R. Synthesis 1989;6:419-423. c) Tewari N, Rohatgi A, Hari Bhushan K, Subramanian GBV. Indian J. Chem. Sect. B 1995;34:851-855.
    • (1983) Angew. Chem. , vol.95 , pp. 810-811
    • Bestmann, H.J.1    Schubert, R.2
  • 28
    • 84985561662 scopus 로고
    • a) Bestmann HJ, Schubert R. Angew. Chem. 1983;95:810-811; Angew. Chem. Int.ed. Engl. 1983;22:780-782. b) Bestmann HJ, Schubert R. Synthesis 1989;6:419-423. c) Tewari N, Rohatgi A, Hari Bhushan K, Subramanian GBV. Indian J. Chem. Sect. B 1995;34:851-855.
    • (1983) Angew. Chem. Int.ed. Engl. , vol.22 , pp. 780-782
  • 29
    • 0001099753 scopus 로고
    • a) Bestmann HJ, Schubert R. Angew. Chem. 1983;95:810-811; Angew. Chem. Int.ed. Engl. 1983;22:780-782. b) Bestmann HJ, Schubert R. Synthesis 1989;6:419-423. c) Tewari N, Rohatgi A, Hari Bhushan K, Subramanian GBV. Indian J. Chem. Sect. B 1995;34:851-855.
    • (1989) Synthesis , vol.6 , pp. 419-423
    • Bestmann, H.J.1    Schubert, R.2
  • 31
    • 0012505048 scopus 로고    scopus 로고
    • EP 818,452;July 9.1996
    • Mane M, Ponge J. EP 818,452;July 9.1996: Chem. Abstr. 1998;128:140564y.
    • (1998) Chem. Abstr. , vol.128
    • Mane, M.1    Ponge, J.2
  • 36
    • 0016697631 scopus 로고
    • a) Schwarz M, Oliver JE, Sonnet PE. J. Org. Chem. 1975;40:2410-2411. b) Jones GB, Huber RS, Mathews JE. Tetrahedron Lett. 1996;37:3643-3646. For NMR data of methyl 7-bromoheptanoate see: c)Pailer M, Gutwillinger H. Monatsh. Chem. 1977;108:1059-1066.
    • (1975) J. Org. Chem. , vol.40 , pp. 2410-2411
    • Schwarz, M.1    Oliver, J.E.2    Sonnet, P.E.3
  • 37
    • 0029930813 scopus 로고    scopus 로고
    • For NMR data of methyl 7-bromoheptanoate see
    • a) Schwarz M, Oliver JE, Sonnet PE. J. Org. Chem. 1975;40:2410-2411. b) Jones GB, Huber RS, Mathews JE. Tetrahedron Lett. 1996;37:3643-3646. For NMR data of methyl 7-bromoheptanoate see: c)Pailer M, Gutwillinger H. Monatsh. Chem. 1977;108:1059-1066.
    • (1996) J. Org. Chem. , vol.37 , pp. 3643-3646
    • Jones, G.B.1    Huber, R.S.2    Mathews, J.E.3    Lett, T.4
  • 38
    • 0013609745 scopus 로고
    • a) Schwarz M, Oliver JE, Sonnet PE. J. Org. Chem. 1975;40:2410-2411. b) Jones GB, Huber RS, Mathews JE. Tetrahedron Lett. 1996;37:3643-3646. For NMR data of methyl 7-bromoheptanoate see: c)Pailer M, Gutwillinger H. Monatsh. Chem. 1977;108:1059-1066.
    • (1977) Monatsh. Chem. , vol.108 , pp. 1059-1066
    • Pailer, M.1    Gutwillinger, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.