A short and efficient synthesis of unnatural ( R)-nicotine

A short and efficient synthesis of unnatural ( R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%)...

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Bibliographic Details
Published inTetrahedron letters Vol. 41; no. 48; pp. 9245 - 9249
Main Authors Girard, Sandrine, Robins, Richard J, Villiéras, Jean, Lebreton, Jacques
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.11.2000
Elsevier
Subjects
alkaloids
allylation
asymmetric synthesis
azides
boron and compounds
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
asymmetric synthesis
boron and compounds
azides
allylation
alkaloids
ALCOHOLS
CHIRAL SYNTHESIS
NICOTINIC ACETYLCHOLINE-RECEPTORS
ORGANOBORANES
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Summary:A short and efficient synthesis of unnatural ( R)-nicotine is described, in which the key step is an intramolecular hydroboration–cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)01675-0