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Volumn 63, Issue 16, 1998, Pages 5473-5482

Studies on the synthesis of chlorothricolide: Diastereo- and enantioselective syntheses of model top-half spirotetronate units

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROTHRICOLIDE;

EID: 0031880505     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980379w     Document Type: Article
Times cited : (16)

References (75)
  • 55
    • 7344267044 scopus 로고    scopus 로고
    • note
    • 1H NMR data with that of the analogous exo cycloadduct in the kijanolide series (ref 47).
  • 62
    • 7344242269 scopus 로고    scopus 로고
    • note
    • Takai olefination of 33 provided the corresponding vinyl iodide as a ca. 5:1 mixture of (E)- and (Z)-vinyl iodide isomers. We elected, therefore, to pursue the synthesis of 12 via a cross-coupling reaction of the dibromoolefin 34 in anticipation that the cross coupling would be highly regioselective (cf. ref 65) and that subsequent reduction of the resulting vinyl bromide would also proceed with good stereocontrol.
  • 64
    • 7344254204 scopus 로고    scopus 로고
    • note
    • Vinylboronic acid 35 was prepared in 71% yield via the reaction of 6-heptyn-1-ol with 2 equiv of catecholborane (neat, 75 °C, 14 h), followed by aqueous workup and Chromatographic purification.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.