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Title

Enantioselective Total Synthesis of Fluvirucinin B1

AuthorsGuignard, Guillaume; Llor, Núria; Molins, Elies ; Bosch, Joan; Amat, Mercedes
Issue Date15-Apr-2016
PublisherAmerican Chemical Society
CitationOrganic Letters 18(8): 1788–1791 (2016)
AbstractA convergent synthesis of fluvirucinin B1 from acid ent-6a and nitrile ent-9, involving an organocopper coupling, a stereoselective allylation, a ring-closing metathesis reaction, and a stereoselective hydrogenation as the key steps, is reported. The starting building blocks have been prepared in a straightforward manner from a common phenylglycinol-derived lactam 1. An unprecedented regioselective oxidation of phenylglycinol-derived secondary amines 5 to carboxylic acids 6 has been developed.
Publisher version (URL)http://dx.doi.org/10.1021/acs.orglett.6b00513
URIhttp://hdl.handle.net/10261/133851
DOI10.1021/acs.orglett.6b00513
ISSN1523-7060
E-ISSN1523-7052
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