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A Glycal Approach to the Synthesis of Steviamine Analogues
Author(s) -
Santhanam Venkatesan,
Ramesh Namakkal G.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402943
Subject(s) - chemistry , glycal , glucal , pyrrolidine , sulfone , glycoside hydrolase , stereochemistry , ethyl acetoacetate , stereoselectivity , organic chemistry , enzyme , catalysis
The synthesis of two new stereoisomers of steviamine, namely 1,8a‐di‐ epi ‐(+)‐steviamine and 2,3‐di‐ epi ‐(–)‐steviamine, is reported, starting from tri‐ O ‐benzyl‐ D ‐glucal. The key step in the synthesis was a modified Julia olefination of a 2‐formyl‐polyhydroxy‐pyrrolidine with a sulfone derived from ethyl acetoacetate. Glycosidase‐inhibition studies revealed that 2,3‐di‐ epi ‐(–)‐steviamine is a selective inhibitor of α‐galactosidase.