The 5-endo-trig cyclization of D-glucose derived gamma-alkenylamines with mercury (II) salts: synthesis of 1-deoxycastanospermine and its 8a-epi-analogue.
The intramolecular aminomercuration of gamma-alkenylamines 1a, 1b and 4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived gamma-alkenylamines 1a and 1b was demonstrated in the synthesis of 1-deoxycastanospermine (3a) and 1-deoxy-8a-epi- castanospermine (3b).
Dhavale
Dilip D
DD
Department of Chemistry, Garware Research Centre, University of Pune, Pune- 411 007, India. ddd@chem.unipune.ernet.in
Jachak
Santosh M
SM
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D005947:Glucose / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry; D008628:Mercury / Q000737:chemistry*
D000470:Alkaloids; D000588:Amines; D007212:Indolizines; C065905:1-deoxycastanospermine; D008628:Mercury; D005947:Glucose