Stereoselective synthesis of the ABC ring system of norzoanthamine.
[reaction: see text] An efficient synthesis of enone 4, representing the ABC ring motif of norzoanthamine, is presented. The crucial C22 quaternary center was introduced via a stereoselective methylation of enone 8. The trans-anti-trans relative configuration of the ABC framework of 4 was installed via a sequence of reactions that included a hydroboration and a modified Robinson annulation.
Ghosh
Subhash
S
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Rivas
Fatima
F
Fischer
Derek
D
González
Miguel A
MA
Theodorakis
Emmanuel A
EA
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D037421:Anthozoa; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*
D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine