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Volumn 1, Issue 11, 1999, Pages 1827-1829

Desymmetrization by ring-closing metathesis leading to 6,8-dioxabicyclo[3.2.1]octanes: A new route for the synthesis of (+)-exo- and endo-brevicomin

Author keywords

[No Author keywords available]

Indexed keywords

BREVICOMIN; FUSED HETEROCYCLIC RINGS; OCTANE; SEX PHEROMONE;

EID: 0033518053     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9910971     Document Type: Article
Times cited : (97)

References (43)
  • 1
    • 0033516491 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Schrock, R. R. Tetrahedron 1999, 55, 8141-8153.
    • (1999) Tetrahedron , vol.55 , pp. 8141-8153
    • Schrock, R.R.1
  • 5
    • 0001962702 scopus 로고    scopus 로고
    • For recent examples, see: (a) Maier, M. E.; Bugl, M. Synlett 1998, 12, 1390-1392.
    • (1998) Synlett , vol.12 , pp. 1390-1392
    • Maier, M.E.1    Bugl, M.2
  • 24
    • 0000119097 scopus 로고
    • and references therein
    • (b) Mori, K. Tetrahedron 1989, 45, 3233-3298 and references therein.
    • (1989) Tetrahedron , vol.45 , pp. 3233-3298
    • Mori, K.1
  • 28
    • 0033582735 scopus 로고    scopus 로고
    • Frontalin, a structurally similar bicyclic acetal, was recently synthesized using ring-closing metathesis as the key step. The retrosynthetic strategy used for (-)-frontalin is distinguished from that which we employed for the brevicomins by a different C-C bond disconnection in the six-membered ring and introduction of the 1(S)-stereocenter via Mukiyama asymmetric allylation or Sharpless asymmetric dihydroxylation. See: Scholl, M.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 1425-1428.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 1425-1428
    • Scholl, M.1    Grubbs, R.H.2
  • 36
    • 85088279751 scopus 로고    scopus 로고
    • 13C NMR data with those reported in ret 17
    • 13C NMR data with those reported in ret 17.
  • 42
    • 85088282933 scopus 로고    scopus 로고
    • 13C NMR data with those reported in ref 18
    • 13C NMR data with those reported in ref 18.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.