Synthesis of polyhydroxylated quinolizidines and azaspiro[4.5]decanes from D-xylose.
The synthesis of novel polyhydroxylated quinolizidines and azaspiro[4.5]decanes is reported. A key step of this transformation involved an addition of allylmagnesium bromide to an ω-bromonitrile derived from D-xylose followed by an intramolecular displacement of a bromide. The resulting cyclic imine was treated either with allylmagnesium bromide or with NaBH4, to provide 2,2-diallyl- or 2-allylpiperidine, respectively. The desired bicyclic framework was constructed via a ring-closing metathesis reaction. The Ru catalysts were reused in the following syn-dihydroxylation step.
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland, and Institute of Physical Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224 Warsaw, Poland.
Michał
M
Malik
Grzegorz
G
Witkowski
Magdalena
M
Ceborska
Sławomir
S
Jarosz
D015394:Molecular Structure; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014994:Xylose / Q000737:chemistry*
D054837:Quinolizidines; D013141:Spiro Compounds; D014994:Xylose