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Volumn 7, Issue 16, 2005, Pages 3497-3500

Synthesis of the bis-spiroacetal moiety of spirolides B and D

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; SPIRO COMPOUND; SPIROLIDE B; SPIROLIDE D;

EID: 23944508520     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051260u     Document Type: Article
Times cited : (52)

References (48)
  • 18
    • 0028284174 scopus 로고
    • Silyl-modified Prins cyclization and the silyl-modified Sakurai cyclization are in fact the same reaction, and the name silyl Prins is adopted herein. See: (a) Marko, I. E.; Bayston, D. J. Tetrahedron 1994, 50, 7141.
    • (1994) Tetrahedron , vol.50 , pp. 7141
    • Marko, I.E.1    Bayston, D.J.2
  • 29
    • 33645393961 scopus 로고    scopus 로고
    • note
    • Optimum solvent was THF, affording 85:15 selectivity in favor of the desired (Z)-7 (69%). The (Z)-configuration of 7 is crucial for the formation of dihydropyran 3, as elimination of the trimethylsilyl group from the resultant six-membered ring formed from the (E)-isomer is very slow (<10% conversion after 12 h).
  • 39
    • 33645417061 scopus 로고    scopus 로고
    • note
    • 19F NMR after formation of the Mosher ester.
  • 44
    • 33645420062 scopus 로고    scopus 로고
    • note
    • Use of a 600 MHz spectrometer was necessary in order to see splitting of the signals.
  • 45
    • 85083243520 scopus 로고
    • For examples of heteroatom-directed Wacker oxidations see: (a) Tsuji, J. Synthesis 1984, 5, 369.
    • (1984) Synthesis , vol.5 , pp. 369
    • Tsuji, J.1
  • 48
    • 33645406369 scopus 로고    scopus 로고
    • note
    • 2O.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.