An efficient total synthesis of (-)-vindoline

Synlett

Volumn , Issue 6, 2000, Pages 883-886

  Kobayashi, Satoshi ^a   Ueda, Toshihiro ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

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;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; PH; REACTION ANALYSIS; TEMPERATURE;

EID: 0034122359     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

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27. 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.