A Glycal Approach to the Synthesis of Steviamine Analogues. Issue 31 (24th September 2014)

• Record Type: Journal Article
• Authors: Santhanam, Venkatesan; Ramesh, Namakkal G.
• Is Part Of: European journal of organic chemistry. Issue 31(2014)
• Page Start: 6992
• Page End: 6999
• Publication Date: 2014-09-24
• Subjects: Natural products -- Nitrogen hetero­cycles -- Alkaloids -- Azasugars -- Carbohydrates -- Biological activity -- Chiral pool; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402943
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: 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. Abstract : We present the synthesis of two new diastereomers of steviamine, an indolizidine alkaloid isolated from Stevia rebaudiana .