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THE STEREOSPECIFIC SYNTHESIS OF (-)-(8R) AND (-)-(8S)-METHYLCANADINE

Abstract:

Regioselective complexation of the dimethoxy arene ring of canadine to the Cr(CO)2 moiety gives two diastereoisomers which are separated by flash chromatography. Deprotonatlon of either diastereoisomer with n-butyllithium followed by addition of methyl iodide or trimethylsilyl chloride gives C11-methyl- or -trimethylsilylcanadine after decomplexatlon. Each diastereoisomer of the C11-trimethylsilylcanadine complex may be treated with base and methyl iodide to give, after desilylation and decom...

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Publication status:
Published

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Journal:
TETRAHEDRON
Volume:
44
Issue:
1
Pages:
171-186
Publication date:
1988-01-01
DOI:
ISSN:
0040-4020
URN:
uuid:e549d099-053e-44b7-9cac-b42f6ce254b1
Source identifiers:
110803
Local pid:
pubs:110803
Language:
English

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