메뉴 건너뛰기




Volumn , Issue 6, 2000, Pages 883-886

An efficient total synthesis of (-)-vindoline

Author keywords

11 hydroxytabersonine; 2,4 dinitrobenzenesulfonamide; Tin mediated indole synthesis; Total synthesis; Vindoline

Indexed keywords

11 HYDROXYTABERSONINE; 2,4 DINITROBENZENESULFONAMIDE; AMINE; ANTINEOPLASTIC AGENT; INDOLE DERIVATIVE; NITROBENZENE DERIVATIVE; TABERSONINE; UNCLASSIFIED DRUG; VINBLASTINE DERIVATIVE; VINDOLINE;

EID: 0034122359     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (84)

References (27)
  • 19
    • 0342281523 scopus 로고    scopus 로고
    • Undesired 1,4-reduction could be avoided by lowering the reaction temperature
    • Undesired 1,4-reduction could be avoided by lowering the reaction temperature.
  • 27
    • 0342716526 scopus 로고    scopus 로고
    • note
    • To a solution of 40 mg (0.105 mmol) of (-)-17β-hydroxy-11-methoxytabersonine 20 in 2.4 ml of 10% methanol/ dichloromethane and 1.8 ml of a saturated aqueous solution of sodium bicarbonate at 0 °C was added 36 mg (0.209 mmol) of m-chloroperoxybenzoic acid. After stirring for 5 min at 0 °C, 0.30 ml (3.56 mmol) of 37% aqueous formaldehyde and 26 mg (0.418 mmol) of sodium cyanoborohydride were added and pH of the solution was adjusted to 3.0 with 10% hydrochloric acid in methanol. After stirring for 5 min, an additional 26 mg (0.418 mmol) of sodium cyanoborohydride was added and stirring was continued at room temperature for 30 min. Sodium carbonate was added to adjust pH of the solution to 9-10 followed by addition of 300 mg of sodium hydrogensulfite. After stirring for 30 min at room temperature, the reaction mixture was partitioned between dichloromethane and dilute ammonium hydroxide. The aqueous layer was thoroughly extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was separated on a preparative TLC to give (-)-deacetylvindoline 22 (27 mg, 64%) as a colorless powder.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.