Synthesis of leucascandrolide A via a spontaneous macrolactolization.
We have developed a concise, convergent, and stereocontrolled synthesis of (+/-)-leucascandrolide A (18 steps from commercially available precursors), featuring a complete relay of the initial stereochemical information via a series of diastereoselective transformations. Spontaneous macrolactolization discovered during this synthetic exercise has provided unprecedented access to this macrolide and demonstrated the possibility of accessing even large-ring systems in a highly controlled and efficient manner.
Wang
Ying
Y
Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Janjic
Jelena
J
Kozmin
Sergey A
SA
D000818:Animals; D007783:Lactones / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D007783:Lactones; D012717:Sesquiterpenes; C408748:leucascandrolide A