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Concise formal synthesis of (-)-peduncularine via ring-closing metathesis
David G Washburn1, Richard W Heidebrecht, Stephen F Martin
1Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Organic Letters
|September 12, 2003
Abstract:
[reaction: see text] A synthesis of the 6-aza[3.2.1]bicyclooctene (-)-2 has been completed by a short sequence of reactions that required only six operations from (S)-malic acid and featured a novel ring-closing metathesis to form the bridged bicyclic ring. Because 2 was previously converted into (-)-peduncularine (1), its preparation constitutes a formal enantioselective synthesis of 1.