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Letters in Organic Chemistry
Volumn 5, Issue 7, 2008, Pages 537-539
Synthesis of a thiophene analog of confusarine
Author keywords

Confusarine; Natural product; Phenanthrene; Photochemistry; Photocyclisation; Thiophene analog
Indexed keywords

EID: 57349195670     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017808785982176     Document Type: Article
Times cited : (1)
References (31)
  • 14
    • 57349200411 scopus 로고    scopus 로고
    • 3 (2.25 g, 8.58 mmol) was added and the solution was heated to 90°C for 30 min. The aldehyde (4) (2.15 g, 6.14 mmol) in DMF (12 mL) and MeOLi (1.6M MeLi in ether, 10 mL) were added to the solution and the mixture was stirred 1h at 90°C. After extraction with AcOEt. the purification by chromatographic column gave cis-(9) (55%, 2.138 g, 4.8 mmmmol) and trans-(9) (10%, 0.381 g, 0.86 mmol).
    • 3 (2.25 g, 8.58 mmol) was added and the solution was heated to 90°C for 30 min. The aldehyde (4) (2.15 g, 6.14 mmol) in DMF (12 mL) and MeOLi (1.6M MeLi in ether, 10 mL) were added to the solution and the mixture was stirred 1h at 90°C. After extraction with AcOEt. the purification by chromatographic column gave cis-(9) (55%, 2.138 g, 4.8 mmmmol) and trans-(9) (10%, 0.381 g, 0.86 mmol).
  • 15
    • 57349086015 scopus 로고    scopus 로고
    • e), 6.87 (s, 1H, H-6), 7.34-7.65 (m, 5H, Ph).
    • e), 6.87 (s, 1H, H-6), 7.34-7.65 (m, 5H, Ph).
  • 16
    • 57349109231 scopus 로고    scopus 로고
    • vinyl).
    • vinyl).
  • 21
    • 57349173911 scopus 로고    scopus 로고
    • +, 100%).
    • +, 100%).
  • 26
    • 57349088660 scopus 로고    scopus 로고
    • A solution of (0.10 g, 0.198 mmol) and DBU (0.122 mL, 0.79 mmol) in THF (25 mL) was irradiated (ERAEUS, TC32, 313 nm) for 2 hours. The reactional mixture was purified by chromatography (silica gel) to give (10) (90%, 650 mg, 1.38 mmol).
    • A solution of (0.10 g, 0.198 mmol) and DBU (0.122 mL, 0.79 mmol) in THF (25 mL) was irradiated (ERAEUS, TC32, 313 nm) for 2 hours. The reactional mixture was purified by chromatography (silica gel) to give (10) (90%, 650 mg, 1.38 mmol).
  • 31
    • 57349123447 scopus 로고    scopus 로고
    • 3, 4,6-Dimethoxy-2-methyl-naphto[2,1,b]thiophen-5-ol: To a solution of naphtalene (0.09 mmol, 0.012 g) in THF (1 mL) was added lithium (0.142 mmol, 1 mg, The mixture was stirred at room temperature for 3 hours. After cooling to -25°C, 10, 65 mg, 0.178 mmol) in THF (2.5 mL) was added dropwise and the solution was stirred for one hour. A saturated ammonium chloride solution (5 mL) was added and the solution was extracted with ethyl acetate. The product was purified by chromatography on silica gel to give (3, 0.160 mmol, 43 mg, 90, 1H-RMN (CDCI3, 300 MHz, 2.70 (s, 3H, J, 1.1 Hz, CH3, 4.02 (s, 3H, OCH3, 4.03 (s, 3H, OCH3, 5.89 (s, 1H, OH, 7.08 (s, 1H, H-6, 7.51 (d, 1H, J, 8 Hz, H-7, 7.66 (d, 1H, J= 8 Hz, H-8, 8.04 (large s, 1H, H-3, 13C-RMN (CDCI3, 75 MHz) 149.7 (C-6, 146.9 (C-2, 141.6 (C-3, 139.5 (C-1a, 138.2 (C-4, 136.8 (C-3a, 132.8 C
    • 3S: 274.0664, found: 274.0663.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.