메뉴 건너뛰기




Volumn 125, Issue 32, 2003, Pages 9576-9577

Macrolactonization via Ti(IV)-mediated epoxy-acid coupling: A total synthesis of (-)-dactylolide [and zampanolide]

Author keywords

[No Author keywords available]

Indexed keywords

ACID; DACTYLOLIDE; EPOXIDE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; ZAMPANOLIDE;

EID: 0043127291     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035579q     Document Type: Article
Times cited : (92)

References (25)
  • 10
    • 0042390695 scopus 로고    scopus 로고
    • note
    • To be described in more detail in a subsequent full report of this work.
  • 12
    • 0037018472 scopus 로고    scopus 로고
    • Related observations of the solvent effect on stereoselectivity of pyran formation have been independently made in the Keck laboratory: (a) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189-1192. For other examples of use of Bronsted acids in related cyclizations, see: (b) Mohr, P. Tetrahedron Lett. 1993, 34, 6251-6254. (c) Cloninger. M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
    • (2002) Org. Lett. , vol.4 , pp. 1189-1192
    • Keck, G.E.1    Covel, J.A.2    Schiff, T.3    Yu, T.4
  • 13
    • 0027376630 scopus 로고
    • Related observations of the solvent effect on stereoselectivity of pyran formation have been independently made in the Keck laboratory: (a) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189-1192. For other examples of use of Bronsted acids in related cyclizations, see: (b) Mohr, P. Tetrahedron Lett. 1993, 34, 6251-6254. (c) Cloninger. M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6251-6254
    • Mohr, P.1
  • 14
    • 0033540691 scopus 로고    scopus 로고
    • Related observations of the solvent effect on stereoselectivity of pyran formation have been independently made in the Keck laboratory: (a) Keck, G. E.; Covel, J. A.; Schiff, T.; Yu, T. Org. Lett. 2002, 4, 1189-1192. For other examples of use of Bronsted acids in related cyclizations, see: (b) Mohr, P. Tetrahedron Lett. 1993, 34, 6251-6254. (c) Cloninger. M. J.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 1092-1093.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1092-1093
    • Cloninger, M.J.1    Overman, L.E.2
  • 15
    • 0032509230 scopus 로고    scopus 로고
    • (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374. For summaries of related work in the oxoammonium salt oxidation arena, see: (b) Rozantsev, E. G. ; Sholle, V. D. Synthesis 1971, 190-202. (c) Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414. (d) Bobbitt, J. M.: Flores, M. C. L. Heterocycles 1988, 27, 509-533. (e) Montanari, F.; Quici, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7, pp 4821-4823.
    • (1998) J. Org. Chem. , vol.63 , pp. 9367-9374
    • Bobbitt, J.M.1
  • 16
    • 84989752057 scopus 로고
    • (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374. For summaries of related work in the oxoammonium salt oxidation arena, see: (b) Rozantsev, E. G. ; Sholle, V. D. Synthesis 1971, 190-202. (c) Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414. (d) Bobbitt, J. M.: Flores, M. C. L. Heterocycles 1988, 27, 509-533. (e) Montanari, F.; Quici, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7, pp 4821-4823.
    • (1971) Synthesis , pp. 190-202
    • Rozantsev, E.G.1    Sholle, V.D.2
  • 17
    • 85012596673 scopus 로고
    • (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374. For summaries of related work in the oxoammonium salt oxidation arena, see: (b) Rozantsev, E. G. ; Sholle, V. D. Synthesis 1971, 190-202. (c) Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414. (d) Bobbitt, J. M.: Flores, M. C. L. Heterocycles 1988, 27, 509-533. (e) Montanari, F.; Quici, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7, pp 4821-4823.
    • (1971) Synthesis , pp. 401-414
    • Rozantsev, E.G.1    Sholle, V.D.2
  • 18
    • 0041936338 scopus 로고
    • (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374. For summaries of related work in the oxoammonium salt oxidation arena, see: (b) Rozantsev, E. G. ; Sholle, V. D. Synthesis 1971, 190-202. (c) Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414. (d) Bobbitt, J. M.: Flores, M. C. L. Heterocycles 1988, 27, 509-533. (e) Montanari, F.; Quici, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7, pp 4821-4823.
    • (1988) Heterocycles , vol.27 , pp. 509-533
    • Bobbitt, J.M.1    Flores, M.C.L.2
  • 19
    • 0041889408 scopus 로고
    • Paquette, L. A., Ed.; John Wiley: Chichester
    • (a) Bobbitt, J. M. J. Org. Chem. 1998, 63, 9367-9374. For summaries of related work in the oxoammonium salt oxidation arena, see: (b) Rozantsev, E. G. ; Sholle, V. D. Synthesis 1971, 190-202. (c) Rozantsev, E. G.; Sholle, V. D. Synthesis 1971, 401-414. (d) Bobbitt, J. M.: Flores, M. C. L. Heterocycles 1988, 27, 509-533. (e) Montanari, F.; Quici, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: Chichester, 1995; Vol. 7, pp 4821-4823.
    • (1995) Encyclopedia of Reagents for Organic Synthesis , vol.7 , pp. 4821-4823
    • Montanari, F.1    Quici, S.2
  • 20
    • 0042891596 scopus 로고    scopus 로고
    • note
    • 2 was the opposite anfipode of that described here. The question of the absolute configuration of natural dactylolide is still open, because the specific rotation of the natural sample differs so greatly from that of each synthetic antipode.
  • 22
    • 0030605887 scopus 로고    scopus 로고
    • Isolation: (a) Tanaka, J.; Higa, T. Tetrahedron Lett. 1996, 37, 5535-5538. Synthesis: (b) Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426-12427 and ref 12b.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 5535-5538
    • Tanaka, J.1    Higa, T.2
  • 23
    • 0035852116 scopus 로고    scopus 로고
    • and ref 12b
    • Isolation: (a) Tanaka, J.; Higa, T. Tetrahedron Lett. 1996, 37, 5535-5538. Synthesis: (b) Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426-12427 and ref 12b.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 12426-12427
    • Smith A.B. III1    Safonov, I.G.2    Corbett, R.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.