Synthesis of the C1'-C11' oxazole-containing side chain of leucascandrolide A. Application of a Sonogashira cross-coupling.
An efficient, convergent synthesis of the C1'-C11' side chain (3) of leucascandrolide A (1) has been achieved. The key bond connection is made through the use of a palladium(0)-catalyzed Sonogashira cross-coupling between trifloyl oxazole (4) and alkynylmetal species (5).
Dakin
Les A
LA
Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA.
Langille
Neil F
NF
Panek
James S
JS
D000480:Alkynes / Q000737:chemistry*; D000818:Animals; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009942:Organometallic Compounds / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D000480:Alkynes; D003432:Cross-Linking Reagents; D009942:Organometallic Compounds; D010080:Oxazoles; D012717:Sesquiterpenes; C408748:leucascandrolide A; D010165:Palladium