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Volumn 5, Issue 5, 2003, Pages 733-736

Formal catalytic asymmetric total synthesis of fostriecin

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FOSTRIECIN; ALKENE; ANTINEOPLASTIC ANTIBIOTIC; PYRONE DERIVATIVE;

EID: 0038798007     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027528o     Document Type: Article
Times cited : (121)

References (40)
  • 3
    • 0036034343 scopus 로고    scopus 로고
    • For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
    • (2002) Curr. Med. Chem. , vol.9 , pp. 2005-2032
    • Lewy, D.S.1    Gauss, C.M.2    Soenen, D.R.3    Boger, D.L.4
  • 4
    • 0037075845 scopus 로고    scopus 로고
    • For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
    • (2002) J. Med. Chem. , vol.45 , pp. 1151-1175
    • McCluskey, A.1    Sim, A.T.R.2    Sakoff, J.A.3
  • 5
    • 0030820773 scopus 로고    scopus 로고
    • For reviews, see: (a) Lewy, D. S.; Gauss, C. M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151-1175. (c) De Jong, R. S.; Mulder, N. H. Anti-Cancer Drugs 1997, 8, 413-418.
    • (1997) Anti-Cancer Drugs , vol.8 , pp. 413-418
    • De Jong, R.S.1    Mulder, N.H.2
  • 13
    • 0035850265 scopus 로고    scopus 로고
    • For synthetic studies of 1, see: (a) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235. (b) Kiyotsuka, Y.; Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2002, 43, 2725-2729.
    • (2001) Org. Lett. , vol.3 , pp. 2233-2235
    • Cossy, J.1    Pradaux, F.2    BouzBouz, S.3
  • 14
    • 0037041358 scopus 로고    scopus 로고
    • For synthetic studies of 1, see: (a) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235. (b) Kiyotsuka, Y.; Igarashi, J.; Kobayashi, Y. Tetrahedron Lett. 2002, 43, 2725-2729.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 2725-2729
    • Kiyotsuka, Y.1    Igarashi, J.2    Kobayashi, Y.3
  • 15
    • 0141662619 scopus 로고    scopus 로고
    • note
    • Jacobsen, Imanishi, Hatakeyama, and Falck utilized Stille or Suzuki cross-coupling for the triene construction. Compound 2 is the common intermediate of Jacobsen, Imanishi, Hatakeyama, and Kobayashi.
  • 17
    • 0141439732 scopus 로고    scopus 로고
    • note
    • Same strategy was employed in Jacobsen's synthesis.
  • 25
    • 0141774515 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 29
    • 0141662617 scopus 로고    scopus 로고
    • note
    • 13C NMR with Imanishi's NMR chart. The stereoselectivity matches that of Yamamoto's transition-state model. AgF-catalyzed reaction in the absence of the chiral ligand resulted in no reaction. Addition of allylmagnesium bromide gave a 1:1 diastereomixture.
  • 30
    • 0141662618 scopus 로고    scopus 로고
    • note
    • The aldol reaction using 7 as a donor proved to be difficult possibly due to a fast retro-aldol reaction. Using 2,2-dimethyl-3-phenylpropanal as a model substrate in a reaction with the lithium enolate derived from 7 gave the product in only 28%. The reaction did not proceed with the zinc enolate. LLB (10 mol %), however, promoted the reaction efficiently, and the product was obtained in 72% yield.
  • 31
    • 0141439731 scopus 로고    scopus 로고
    • note
    • Diastereoisomers could not be separated at this stage. The relative configuration of C-8 and C-9 was determined by NOE measurement on acetonide 22.
  • 32
    • 0141439730 scopus 로고    scopus 로고
    • note
    • 2O and 72% ee with LLB.
  • 34
    • 0141439729 scopus 로고    scopus 로고
    • note
    • Other diastereomers ((9S, 11S)- and (9S, 11R)- derived from 18b) were separable at this stage (14 and 4%, respectively). The relative configuration of C-9 and C-11 was determined by NOE measurement. See Supporting Information for details.
  • 39
    • 0141551232 scopus 로고    scopus 로고
    • note
    • Absolute configuration of 24 was confirmed comparing the sign of the optical rotation to the reported data by Hatakeyama. Two steps (phosphate ester formation and deprotection) are necessary from 24 to 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.