An alternative synthesis of 1,1'-bis-valienamine from D-glucose.
An alternative synthesis of 1,1'-bis-valienamine 5, which was demonstrated to be a potent trehalase inhibitor, has been achieved from d-glucose in 12 steps with 15% overall yield via enone 12 as the key intermediate, involving a direct aldol reaction of a glucose-derived diketone and a palladium-catalyzed allylic coupling reaction as the key steps.
Shing
Tony K M
TK
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, Hong Kong. tonyshing@cuhk.edu.hk
Cheng
Hau M
HM
D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000737:chemistry*; D006595:Hexosamines / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism; D014198:Trehalase / Q000037:antagonists & inhibitors
C551747:1,1'-bis-valienamine; D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D006595:Hexosamines; D014198:Trehalase; D005947:Glucose