Studies on the synthesis of valienamine and 1-epi-valienamine starting from D-glucose or L-sorbose.
Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either D-glucose or L-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
Cumpstey
Ian
I
Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden.
Gehrke
Sebastian
S
Erfan
Sayeh
S
Cribiu
Riccardo
R
D053138:Cyclohexenes / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D006595:Hexosamines / Q000138:chemical synthesis*; D013013:Sorbose / Q000737:chemistry*; D013237:Stereoisomerism
D053138:Cyclohexenes; D006595:Hexosamines; C030791:valienamine; D005947:Glucose; D013013:Sorbose