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Volumn 5, Issue 4, 1999, Pages 1172-1175

Efficient synthesis of 11-cis-retinoids

Author keywords

11 cis retinoids; Chromophores; Enynes; Hydrogenations; Retinal analogues; Zinc reductions

Indexed keywords

RETINOID;

EID: 0032922518     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990401)5:4<1172::AID-CHEM1172>3.0.CO;2-Q     Document Type: Article
Times cited : (37)

References (37)
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    • Rando, R.R.1
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    • R. R. Rando, Angew. Chem. 1990, 102, 507-526; Angew. Chem. Int. Ed. Engl. 1990, 29, 461-480.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 461-480
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    • J. Uenishi, R. Kawahama, O. Yonemitsu, A. Wada, M. Ito, Angew. Chem. 1998, 110, 334-336; Angew. Chem. Int. Ed. 1998, 37, 320-323.
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    • note
    • The vinyl iodide 9 was obtained by reduction of 2-butyne-1-ol mediated by titanocene dichloride (ref. [35]). Subsequent quenching with iodine was followed by protection of the primary alcohol with tributyldimethylsilyl chloride.
  • 35
    • 0344954778 scopus 로고    scopus 로고
    • note
    • The reduction of 11a and 11b was much more sensitive to the quality of the catalyst. Slight contamination such as trace acid led to isolation of mostly rrans-reduced product. To obtain good stereoselectivity, the solvents used for preparation and washing of the zinc catalyst were of highest purity. The catalyst was not allowed to dry in air during preparation, and oxygen was excluded during the reduction. Interestingly, the reduction of 10b is not as sensitive and is much more forgiving, as it occurs with very high stereoselectivity.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.