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Volumn 48, Issue 38, 2007, Pages 6722-6725

Enantioselective synthesis of 2-[(3-ethyl-4-piperidyl)methyl]indoles from a phenylglycinol-derived lactam: formal synthesis of Strychnos alkaloids

Author keywords

Indoles; Oxazolopiperidone lactams; Phenylglycinol; Piperidines; Strychnos alkaloids

Indexed keywords

2 [(3 ETHYL 4 PIPERIDYL)METHYL]INDOLE; ALKALOID; INDOLE DERIVATIVE; LACTAM; PHENYLGLYCINE; UNCLASSIFIED DRUG;

EID: 34548028977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.079     Document Type: Article
Times cited : (9)

References (38)
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    • For synthetic routes to racemic cis-1b, see Refs. 1a,b.
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    • For a recent review on 1,3-dithianes in natural product synthesis, see:
    • For a recent review on 1,3-dithianes in natural product synthesis, see:. Yus M., Nájera C., and Foubelo F. Tetrahedron 59 (2003) 6147-6212
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    • note
    • 4Cl, and extracted with EtOAc. The combined organic extracts were dried and concentrated, and the resulting residue was chromatographed (9:1 to 1:4 hexane-EtOAc) to give compounds cis-4 (2.58 g, 73%) and trans-4 (0.60 g, 17%). Operating as above (reaction conditions: 16 h at room temperature), from dithiane 2 (2.33 g, 9.9 mmol) and lactam 3 (2 g, 8.2 mmol) was obtained trans-4 (3.6 g, 93%) after flash chromatography.
  • 38
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    • note
    • 2 ind), 38.9 (C-4), 39.1 (C-3), 43.5 (C-6), 47.0 (C-2), 100.3 (C-3 ind), 110.6 (C-7 ind), 119.4 and 119.6 (C-4 and C-5 ind), 120.8 (C-6 ind), 128.7 (C-3a ind), 135.9 (C-2 ind), 136.7 (C-7a ind).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.