Total synthesis of (-)- and (+)-dysibetaine.
Glycidamides 6R and 6S were elaborated to (R,R)- and (S,S)-dysibetaines (1R and 1S) by intramolecular alkylation and functional group modification in 23% overall yield. The absolute stereochemistry of natural dysibetaine was established as S,S by comparison of the optical rotation of the natural product with that of the synthetic materials.
Snider
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BB
Department of Chemistry, MS015, Brandeis University, Waltham, Massachusetts 02454-9110, USA. snider@brandeis.edu
Gu
Y
Y
D000478:Alkylation; D000818:Animals; D018360:Crystallography, X-Ray; D018690:Excitatory Amino Acid Agonists / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D018690:Excitatory Amino Acid Agonists; D011760:Pyrrolidinones; C431075:dysibetaine