First asymmetric total synthesis of (-)-(R)- and (+)-(S)-geibalansine

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 9-10

  Morel, Ademir F ^a   Larghi, E L ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

(1,4 DI TERT BUTYLSALICYLIDENE)DIAMINOCYCLOHEXANE MANGANESE CHLORIDE; ALKALOID; BLEACHING AGENT; BUFFER; CHROMENE DERIVATIVE; EPOXIDE; GUIBALANSINE; MANGANESE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL ANALYSIS; CHIRALITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POLARIMETRY; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 0347418212     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.09.052     Document Type: Article

References (16)

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11. 3N in hexanes and then, was washed with hexanes prior to use.
12. 4. The volatiles were removed in vacuo, and flash chromatographed in silica 200-400 mesh, eluting with mixtures of hexanes/AcOEt. The epoxides were obtained in pure forms (90-95% isolated yield), and ee <93%, estimated by polarimetry. Synthesis of (-)-(R)-geibalansine
13. 4. The volatiles were removed in vacuo, and flash chromatographed in silica 200-400 mesh, eluting with mixtures of hexanes/AcOEt. The epoxides were obtained in pure forms (90-95% isolated yield), and ee >93%, estimated by polarimetry. Synthesis of (-)-(R)-geibalansine
14. 1: A solution of (+)-(R,R)-epoxide
15. -1. The (S)-eluted before the (R)-form, with
16. -1. The (S)-eluted before the (R)-form, with (-)-(R)-1 being obtained with ee of 94%.