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Volumn 13, Issue 18, 2002, Pages 1965-1967

Progress towards the decalin portion of (+)-compactin

Author keywords

[No Author keywords available]

Indexed keywords

BORON; COMPACTIN; DECALIN; ESTER DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; TETRALIN DERIVATIVE;

EID: 0037145029     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00570-0     Document Type: Article
Times cited : (7)

References (16)
  • 14
    • 84992543056 scopus 로고    scopus 로고
    • All new compounds reported had spectral data in accord with the assigned structure and gave satisfactory elemental analyses and/or high resolution mass spectral data
    • All new compounds reported had spectral data in accord with the assigned structure and gave satisfactory elemental analyses and/or high resolution mass spectral data.
  • 15
    • 84992543067 scopus 로고    scopus 로고
    • note
    • Preparation of (1S,2S)-8-methoxy-2-methyl-1-vinyl-1,2,3,4-tetrahydronaphthalene 14: Methyl lithium (1.4 M, 2.85 ml, 4 mmol) was added to a solution of tetravinyl tin (0.240 g, 1 mmol) in tetrahydrofuran (5 ml) at 0°C and stirred for 20 min. The temperature was then cooled to -78°C and copper cyanide (0.190 g, 2 mmol) was added. After 20 min, compound 12 (0.211 g, 0.7 mmol) was added and the reaction mixture was warmed to -30°C. After 10 min the reaction mixture as warmed to 0°C and stirred for 25 min. The reaction mixture was quenched in 1 M HCl. The suspension was extracted with ethyl acetate, dried with magnesium sulfate filtered and concentrated. The residue was purified by flash chromatography to yield 0.153 g (55% for the two steps). Compound 13 (0.153 g, 0.8 mmol) was dissolved in DMF (1 mL), cooled to 0°C, and sodium hydride (0.019 g, 0.8 mmol) was added. The solution was stirred for 10 min, after which time an excess of methyl iodide was added. The mixture was then brought to room temperature. Quenched with water and the product extracted with ether. The residue was purified by flash chromatography to yield 14 (0.149 g, 91%) (de=90% by HPLC Chiralcel AD column using 10% hexane/isopropanol).
  • 16
    • 84992543065 scopus 로고    scopus 로고
    • note
    • ++1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.