Synthesis of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids from D-glycals.
New syntheses of (-)-deoxoprosophylline, (+)-2-epi-deoxoprosopinine, and (2R,3R)- and (2R,3S)-3-hydroxypipecolic acids are reported. Utilization of the chiral functionalities of Perlin aldehydes, derived from 3,4,6-tri-O-benzyl glycals, has been done along with chemoselective saturation of olefins and reductive aminations as key steps.
Department of Chemistry, Indian Institute of Technology Kanpur 208 016, India.
Hari Prasad
HP
Kokatla
Rima
R
Lahiri
Pavan K
PK
Kancharla
Venkata Ramana
VR
Doddi
Yashwant D
YD
Vankar
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
C530277:2-hydroxymethyl-6-dodecylpiperidin-3-ol; C529304:3-hydroxypipecolic acid; D000470:Alkaloids; D001593:Benzyl Compounds; D010875:Pipecolic Acids; D010880:Piperidines; D011714:Pyrans; C445731:deoxoprosopinine