16473-12-4Relevant articles and documents
Synthesis and chiroptical properties of methanocycloocta[6]indoles
Butkus, Eugenius,Berg, Ulf,Malinauskiene.t, Jule,Sandstroem
, p. 1353 - 1358 (2000)
The synthesis of chiral methanocyclocta[6]indoles, the fused structures obtained from enantiomeric bicyclo[3.3.1]nonanones via Fisher indolization reaction, is reported. The starting optically active bicyclo[3.3.1]nonane-2,6-dione (1) was obtained by a chiral HPLC enantiomer separation on a swollen microcrystalline triacetylcellulose column and by the enzymatic resolution of the racemic dione. The circular dichroism (CD) spectra of the chiral structures 4, 5, and 7 were recorded, and the absolute configuration for the indole compounds was assigned. The theoretical calculations of the CD spectrum of diindole 4 reproduce the aBb couplet at 229 nm but predict wrong signs for the 1La and 1Lb bands using standard polarization directions. The CD spectrum of indole ketone 5 is reproduced correctly.
SYNTHESIS OF 1-HYDROXY-2-(N-SUBSTITUTED)AZATWISTANES
Kadzyauskas, P. P.,Malinauskene, Yu. A.,Butkus, E. P.,Zefirov, N. S.
, p. 727 - 729 (2007/10/02)
The reductive amination of bicyclononane-2,6-dione with benzylamine or isopropylamine in the presence of sodium borohydride proceeds with the formation of 1-hydroxy-2-(N-substituted)azatwistanes.When 1-hydroxy-2-benzyl-2-azatwistane is refluxed with acetic anhydride, the ring is opened to give 2-acetoxy-6-acetylbenzylaminobicyclononane.The structures of the synthesized compounds were proved by means of the IR and PMR spectra and the results of elementary analysis.
