Stereoselective synthesis of (+)-boronolide.
The delta-lactone boronolide (+)-1, a pharmacologically active, naturally occurring product, has been synthesized in enantiopure form with L-erythrulose as the chiral starting material. The key steps of the synthesis were a highly stereoselective aldol-reduction one-pot sequence, an indium-mediated diastereoselective aldehyde allylation, and a ring-closing metathesis.
U. P. de Química Inorgánica y Orgánica, Universidad Jaume I, E-12080 Castellón, Spain.
Miguel
M
Carda
Santiago
S
Rodríguez
Beatriz
B
Segovia
J Alberto
JA
Marco
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis*; D019686:Lamiaceae / Q000737:chemistry; D008270:Madagascar; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism; D013780:Tetroses / Q000737:chemistry
D007783:Lactones; D013780:Tetroses; C469612:boronolide; C100073:erythrulose