Application of intramolecular 1,3-dipolar cyclic addition of azide and olefin; construction of (pyrrolidine-2-ylidene)glycinate and glycinamides.
Oxopropyl E-(pyrrolidine-2-ylidene)glycinamide (5c) and allyl E-(pyrrolidine-2-ylidene)glycinate (5d) were effectively synthesized from 2,3,5-tri-O-benzyl-4-O-tert-butyldimethylsilyl(TBDMS)-D-arabinal (7) using intramolecular 1,3-dipolar cyclic reaction of azide and olefin as a key reaction. These results proved this cyclic reaction should be applicable for the synthesis of various (pyrrolidine-2-ylidene)glycinate and glycinamide. In addition, the development of a synthetic route for the precursor of an unsaturated cyclic dehydro amino acid involved in azinomycins (carzinophilin) using relating glycinate, methyl E-(pyrrolidine-2-ylidene)glycinate (5a) was described.
Konda-Yamada
Yaeko
Y
School of Pharmaceutical Sciences, Kitasato University, Shirokane, Tokyo 108-8641, Japan. konday@pharm.kitasato-u.ac.jp
Asano
Keiko
K
Satou
Takahiro
T
Monma
Souichi
S
Sakayanagi
Masataka
M
Satou
Noriko
N
Takeda
Kazuyoshi
K
Harigaya
Yoshihiro
Y
D000475:Alkenes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry; D011759:Pyrrolidines / Q000737:chemistry*
D000475:Alkenes; D001386:Azides; D011759:Pyrrolidines; C018556:glycine amide; D005998:Glycine