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Volumn 124, Issue 51, 2002, Pages 15196-15197

Intramolecular silicon-assisted cross-coupling: Total synthesis of (+)-brasilenyne

Author keywords

[No Author keywords available]

Indexed keywords

BRASILENYNE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

EID: 0037176244     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028936q     Document Type: Article
Times cited : (80)

References (38)
  • 1
    • 0000359232 scopus 로고
    • Scheue,r P. J., Ed.; Academic Press: New York
    • (a) Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; Vol. 5, pp 131-257.
    • (1983) Marine Natural Products , vol.5 , pp. 131-257
    • Erickson, K.L.1
  • 3
    • 0000109030 scopus 로고
    • (a) For a review of construction of medium-ring ethers, see: Elliott. M. C. Contemp. Org. Synth. 1994. 1, 457.
    • (1994) Contemp. Org. Synth. , vol.1 , pp. 457
    • Elliott, M.C.1
  • 4
    • 0012187728 scopus 로고    scopus 로고
    • Synthesis of marine natural products containing polycyclic ethers
    • (b) Hirama, M.; Rainder, J. D.; Eds. Synthesis of marine natural products containing polycyclic ethers. Tetrahedron Symposium in Print No. 90 2002, 58, 1779-2040.
    • (2002) Tetrahedron Symposium in Print No. 90 , vol.58 , pp. 1779-2040
    • Hirama, M.1    Rainder, J.D.2
  • 13
    • 0012188051 scopus 로고    scopus 로고
    • note
    • The parent 2,3,4,9-tetrahydrooxonin ring is unknown.
  • 15
    • 0012183077 scopus 로고    scopus 로고
    • note
    • L-(S)-Malic acid was purchased from Aldrich and was shown to be of 99% ee by CSP-GLC analysis.
  • 16
    • 0012113481 scopus 로고    scopus 로고
    • note
    • All new compounds have been fully characterized, and all yields correspond to isolated, analytically pure materials. For detailed experimental procedures, see Supporting Information.
  • 17
    • 33845550948 scopus 로고
    • To the best of our knowledge, the ring opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene is unprecedented. Ring opening of acetal templates with silylacetylenic compounds promoted by Lewis acid have been reported, see: (a) Johnson, W. S.; Elliott, R.; Elliott, J. D. J. Am. Chem. Soc. 1983, 105, 2904.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2904
    • Johnson, W.S.1    Elliott, R.2    Elliott, J.D.3
  • 21
    • 0012183078 scopus 로고    scopus 로고
    • note
    • 8), whose full stereostructure was confirmed by single-crystal X-ray diffraction. The crystallographic coordinates of the cobalt complex have been deposited with the Cambridge Crystallographic Data Centre; deposition no. CCDC-195245.
  • 28
    • 0001057466 scopus 로고
    • For addition of allyltributylstannes to α-alkoxy aldehydes, see: Keck, G. E.; Boden, E. P. Tetrahedron Lett. 1984, 25, 265.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 265
    • Keck, G.E.1    Boden, E.P.2
  • 31
    • 33751392358 scopus 로고
    • Schrock's molybdenum complex is commercially available (Strem) or can be prepared according to the reported procedure with consistent purity and reactivity, see: (a) Fox, H. H.; Yap, K. B.; Robbins, J.; Cai, S.; Schrock, R. R. Inorg. Chem. 1992, 31, 2287.
    • (1992) Inorg. Chem. , vol.31 , pp. 2287
    • Fox, H.H.1    Yap, K.B.2    Robbins, J.3    Cai, S.4    Schrock, R.R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.