Convergent Total Synthesis of Lamellarins and Their Congeners
Morikawa Daiki, Kazuki Morii, Yuto Yasuda, Atsunori Mori, Kentaro Okano
Abstract
A convergent total synthesis of lamellarins S and Z is described. The synthesis features a halogen dance of an easily accessible α,β-dibromopyrrole promoted by an ester moiety. The resultant β,β'-dibromopyrrole undergoes a ligand-controlled Suzuki-Miyaura coupling to provide a range of diarylated pyrrole derivatives. The established synthetic method was also applicable to the synthesis of ningalin B and lukianols A and B.
Topics & Concepts
MoietyConvergent synthesisTotal synthesisPyrroleLigand (biochemistry)ChemistrySuzuki reactionStereochemistryCombinatorial chemistryOrganic chemistryReceptorBiochemistryAlkylArylSynthesis and Characterization of PyrrolesPorphyrin and Phthalocyanine ChemistryMarine Sponges and Natural Products