Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 11, Pages 4628-4634Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200567n
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Funding
- Noramco, Inc.
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- Canada Foundation for Innovation (CFI)
- Reasearch Corporation
- TDC Research, Inc.
- TDC Research Foundation
- Brock University
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Buprenorphine was synthesized from oripavine by a sequence involving the conversion of oripavine into its cyclopropylmethyl quaternary salt, N-demethylation with thiolate to N-cyclopropylmethyl nororipavine, and conversion of this material to the title compound by previously available methods. The new synthesis avoids toxic reagents used previously, is shorter, and proceeds in comparable yields. Experimental and spectral data are provided for all new compounds.
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