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Synlett
Volumn , Issue 2, 2007, Pages 324-326
Iminophosphorane-based preparation of 2,5-disubstituted oxazole derivatives: Synthesis of the marine alkaloid almazole C
Author keywords

aza Wittig reaction; Iminophosphoranes; Indoles; Marine alkaloids; Oxazoles
Indexed keywords

ALKALOID DERIVATIVE; ALMAZOLE C; ALPHA AZIDOACETYL INDOLE; CHLORIDE; IMINOPHOSPHORANE; INDOLE; OXAZOLE DERIVATIVE; PHTHALOYLPHENYLALANYL CHLORIDE; UNCLASSIFIED DRUG;
EID: 33847025693     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967995     Document Type: Article
Times cited : (22)
References (42)
  • 28
    • 17844376761 scopus 로고    scopus 로고
    • (b) Eguchi, S. ARKIVOC 2005, (ii), 98.
    • (2005) ARKIVOC , vol.2 , pp. 98
    • Eguchi, S.1
  • 39
    • 33847070794 scopus 로고    scopus 로고
    • 2, S)-1-{5-[N-(Methoxymethyl, 1H-indol-3-yl]oxazol-2-yl}-2-phenylethyl]isoindoline-1,3-dione (7, To a solution of 3-(α-azidoacetyl) indole 5 (0.2 g, 0.82 mmol) in dry THF (32 mL, n-tributylphosphine (0.3 mL, 1.23 mmol) was added dropwise at 0°C under N2. Then, a solution of (S)-N-phthaloylphenylalanyl chloride 6 (0.26 g, 0.82 mmol) in the same solvent (20 mL) was added. The resultant mixture was stirred at r.t. for 1 h, and then dry Et3N (0.17 mL, 1.23 mmol) was added and stirred for 2 h. The resultant solution was concentrated to dryness under reduced pressure and the residue was chromatographed on a silica gel column using CH 2Cl2-EtOAc (8:2) as eluent to give 7 (0.27 g, 70% yield, Mp 157-160°C 1H NMR (300 MHz, CDCl3, α, 3.17 (s, 3 H, OCH3, 3.79 (m, 2 H, CH2, 5.37 s, 2 H, OCH 2
    • 4: C, 72.94; H, 4.85; N, 8.80. Found: C, 72.86; H, 4.80; N, 8.85.
  • 42
    • 33847082845 scopus 로고    scopus 로고
    • Almazole C (1, To a suspension of 7 (0.32 g, 0.68 mmol) in EtOH (20 mL, hydrazine monohydrate (0.14 mL, 2.68 mmol) was added at 0°C. The reaction mixture was stirred for 36 h at r.t. The precipitated solid was separated by filtration, slurried with CH2Cl2 and filtered. The filtrate was dried (MgSO4) and the solvent removed under reduce pressure to give (S)-1-{5-[N-(Methoxymethyl)-1 H-indol-3-yl]oxazol-2-yl}-2-phenylethanamine (8, 0.21 g, 90% yield, A mixture of the amine 8 (0.4 g, 1,16 mmol, formaldehyde 37, 0.86 mL, 9.54 mmol) and 10% Pd on charcoal (0.24 g, 2.3 mmol) in EtOH (25 mL) was stirred at r.t. under nitrogen for 17 h. The reaction mixture was filtered under celite and the solvent removed under reduce pressure to give (S)-1-{5-[1-(methoxymethyl)-1H-indol-3-yl]oxazol-2-yl}-N, N-dimethyl-2-phenylethanamine 9, 0.388g, 90% yield, A mixture of N-methoxymethyl al
    • 20 +141 (c 0.1, MeOH)} were identical to natural almazole C.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.