A practical asymmetric synthesis of the ACNO fragment of morphine alkaloids

Synlett

Volumn , Issue 15, 2008, Pages 2299-2302

  Hsin, Ling Wei ^a   Chang, Li Te ^a   Liou, Huei Ling ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Asymmetric catalysis; Heck reaction; Hydrogenation; Total synthesis; Transition metals

Indexed keywords

MORPHINE; MORPHINE DERIVATIVE; PALLADIUM; PLATINUM; RUTHENIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HECK REACTION; HYDROGENATION; RACEMIZATION;

EID: 52949100215     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078021     Document Type: Article

References (23)

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21. Chiral HPLC Analysis: The free base of the sample was dissolved in 1% isopropanol (IPA) in n-hexane. Then the sample solution (10 μL) was eluted using 1.5% [for compound (+)-4], 2.5% [for compounds (-)-3 and (-)-6], or 8% [for compound (-)-10] IPA in n-hexane in the presence of 0.2% diethylamine as mobile phase on the CHIRALCEL OD column (250 x 4 mm, DAICEL). The ee values were calculated based on the UV absorption (λ = 254 nm) areas of the two enantiomers.
22. Microwave Experiments: The reactions under microwave irradiation were conducted in sealed heavy-walled Pyrex tubes. Microwave heating was carried out with a single mode cavity Discover Microwave Synthesizer (CEM Corporation, P.O. Box 200, Matthews, NC 28106, USA), producing continuous irradiation at 2.45 GHz. The reaction temperature was measured and feedback controlled with an infrared device under the reaction vessel.
23. 2: 271.1572; found: 271.1569.