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Volumn 3, Issue 12, 2006, Pages 922-925

Crotylation of (R)-2,3-cyclohexylideneglyceraldehyde: A simple strategy for the synthesis of enantiopure anti-alzheimer (R)-arundic acid

Author keywords

(R) 2,3 cyclohexylideneglyceraldehyde; Alzheimer disease; Arundic acid; Crotylation; Enantiopurity; Ozonolysis; Propargyl alcohol; Stereoselectivity

Indexed keywords


EID: 33846696745     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806779468059     Document Type: Article
Times cited : (11)

References (53)
  • 4
    • 0002213778 scopus 로고    scopus 로고
    • and references cited therein
    • b) Thomas, E. J. Chem. Commun., 1997, 411 and references cited therein;
    • (1997) Chem. Commun. , pp. 411
    • Thomas, E.J.1
  • 42
    • 33846692057 scopus 로고    scopus 로고
    • note
    • 3 (4.9 g, 0.03 mol)] in THF (70 mL) was added Zn dust (2.25 g, 0.035 mol for Co and Cu; 1.95 g, 0.03 mol for Fe) in portions over a period of 15 min. The mixture was stirred at the ambient temperature for the period as shown in Table 1. The reaction mixture was then treated successively with water (50 mL) and EtOAc (100 mL), stirred for 10 min more and then filtered. The filtrate was treated with 2% aqueous HCl to dissolve a little amount of suspended particles. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, brine and then dried. Solvent removal and column chromatography of the residue (silica gel, 0-15% EtOAc in petroleum ether) 7a [19], 7b [20] and 7c [21] in pure form and the diastereomeric ratios in all cases were determined based on their isolated yields after column chromatography as shown in Table 1.
  • 43
    • 33846684038 scopus 로고    scopus 로고
    • note
    • 13C NMR: δ 14.06, 22.61, 23.78, 23.99, 25.09, 27.13, 29,21, 31.30, 31.75, 35.01, 36.39, 47.20, 65.63, 74.88, 76.37, 109.84, 116.70, 138.08.
  • 44
    • 33846669192 scopus 로고    scopus 로고
    • note
    • 13C NMR: δ 13.95, 22.53, 23.67, 23.84, 24.89, 26.66, 29,20, 30.33, 31.71, 34.82, 36.02, 47.52, 63.37, 72.50, 76.47, 109.01, 116.67, 138.50.
  • 45
    • 33846691653 scopus 로고    scopus 로고
    • note
    • 13C NMR: δ 14.04, 22.60, 23.78, 23.95, 25.12, 27.07, 29,21, 30.96, 31.75, 34.85, 36.31, 46.39, 65.40, 73.91, 76.40, 109.03, 117.46, 137.92.
  • 49
    • 33846678808 scopus 로고    scopus 로고
    • note
    • 4.
  • 50
    • 33846655187 scopus 로고    scopus 로고
    • note
    • 13C NMR: δ 14.04, 22.59, 27.01, 29.27, 31.78, 35.61, 38.18, 40.45, 67.17, 70.08, 115.27, 142.47.
  • 52
    • 33846694132 scopus 로고    scopus 로고
    • note
    • 2).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.