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Volumn 68, Issue 8, 2003, Pages 3216-3224

Stereoselective synthesis of cyclic ethers by intramolecular trapping of dicobalt hexacarbonyl-stabilized propargylic cations

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC COMPOUNDS;

EID: 0037453693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0340556     Document Type: Article
Times cited : (36)

References (41)
  • 7
    • 0019790981 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6773-6775
    • Lin, Y.-Y.1    Risk, M.2    Ray, S.M.3    Van Engen, D.4    Clardy, J.5    Golik, J.6    James, J.C.7    Nakanishi, K.8
  • 8
    • 33845374592 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 514-515
    • Shimizu, Y.1    Chou, H.-N.2    Bando, H.3    VanDuyne, G.4    Clardy, J.C.5
  • 9
    • 0001418722 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6476-6477
    • Krishna Prasad, A.V.1    Shimizu, Y.K.2
  • 10
    • 0025045174 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4380-4386
    • Murata, M.1    Legrand, A.M.2    Ishibashi, Y.3    Fukui, M.4    Yasumoto, T.5
  • 11
    • 0026630275 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1992) J. Org. Chem. , vol.57 , pp. 5448-5453
    • Nagai, H.1    Murata, M.2    Torigoe, K.3    Satake, M.4    Yasumoto, T.5
  • 12
    • 0000670453 scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 361-362
    • Satake, M.1    Murata, M.2    Yasumoto, T.3
  • 13
    • 0030070097 scopus 로고    scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 479-480
    • Igarashi, T.1    Satake, M.2    Yasumoto, T.3
  • 14
    • 0030433808 scopus 로고    scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1996) Biosci. Biotech. Biochem. , vol.60 , pp. 2103-2105
    • Satake, M.1    Ishibashi, Y.2    Legrand, A.-M.3    Yasumoto, T.4
  • 15
    • 0030581419 scopus 로고    scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5955-5958
    • Satake, M.1    Terasawa, K.2    Kadowaki, Y.3    Yasumoto, T.4
  • 16
    • 0032569872 scopus 로고    scopus 로고
    • Representative examples of marine ladder toxins. (a) Brevetoxin-B: Lin, Y.-Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc. 1981, 103, 6773-6775. (b) Brevetoxin-A: Shimizu, Y.; Chou, H.-N.; Bando, H.; VanDuyne, G.; Clardy J. C. J. Am. Chem. Soc. 1986, 108, 514-515. (c) Hemibrevetoxin-B: Krishna Prasad, A. V.; Shimizu, Y. K. J. Am. Chem. Soc. 1989, 111, 6476-6477. (d) Ciguatoxin: Murata, M.; Legrand, A. M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380-4386. (e) Gambieric acids: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. (f) Gambierol: Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361-362. (g) Prymnesin-2: Igarashi, T.; Satake, M.; Yasumoto, T. J. Am. Chem. Soc. 1996, 118, 479-480. (h) Scaritoxin: Satake, M.; Ishibashi, Y.; Legrand, A.-M.; Yasumoto, T. Biosci. Biotech. Biochem. 1996, 60, 2103-2105 (i) Yessotoxin: Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett. 1996, 37, 5955-5958. (j) Adriatoxin: Ciminello, P.; Fattorusso, E.; Forino, M.; Magno, S.; Poletti, R.; Viviani, R. Tetrahedron Lett. 1998, 39, 8897-8900.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8897-8900
    • Ciminello, P.1    Fattorusso, E.2    Forino, M.3    Magno, S.4    Poletti, R.5    Viviani, R.6
  • 20
    • 0032532258 scopus 로고    scopus 로고
    • (d) Hoberg, L. O. Tetrahedron 1998, 54, 12631-12670.
    • (1998) Tetrahedron , vol.54 , pp. 12631-12670
    • Hoberg, L.O.1
  • 33
    • 0001780886 scopus 로고    scopus 로고
    • Paquette, L. A., et al., Eds.; Wiley: New York
    • Katsuki, T.; Martín, V. S. Organic Reactions; Paquette, L. A., et al., Eds.; Wiley: New York, 1996; Vol. 48, pp 1-299.
    • (1996) Organic Reactions , vol.48 , pp. 1-299
    • Katsuki, T.1    Martín, V.S.2
  • 38
    • 0344773097 scopus 로고    scopus 로고
    • note
    • The stereochemistry was clarified by NOE studies over 24c and 24b and by chemical transformation to the diastereoisomers 24d and 24e (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.