Concise synthesis of iminocyclitols via Petasis-type aminocyclization.
A two-step method has been developed to synthesize several biologically important iminocyclitols in ca. 44-60% yields by using Petasis-type condensation. The method is very general and operationally simple, affording a series of iminocyclitols from easily available sugar derivatives. Unexpected diastereoselectivities are observed, suggesting that the condensation may proceed through a five- or six-membered cyclic iminium ion intermediate.
Hong
Zhangyong
Z
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Liu
Lei
L
Sugiyama
Masakazu
M
Fu
Yu
Y
Wong
Chi-Huey
CH
D000606:Amino Sugars / Q000138:chemical synthesis / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D054812:Cyclitols / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D050111:Imino Sugars / Q000138:chemical synthesis / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry
D000606:Amino Sugars; D001897:Boronic Acids; D054812:Cyclitols; D050111:Imino Sugars; D010880:Piperidines; D011759:Pyrrolidines