Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.
[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.
Washburn
David G
DG
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA.
Heidebrecht
Richard W
RW
Martin
Stephen F
SF
D000470:Alkaloids / Q000138:chemical synthesis*; D001372:Aza Compounds / Q000138:chemical synthesis; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D001372:Aza Compounds; D001643:Bridged Bicyclo Compounds; D026121:Indole Alkaloids; D007211:Indoles; D008293:Malates; C467792:peduncularine; C030298:malic acid