Enantioselective Total Synthesis of (+)-Amphirionin-4.
An enantioselective total synthesis of (+)-amphirionin-4 has been accomplished in a convergent manner. The synthesis features an efficient enzymatic lipase resolution to access the tetrahydrofuranol core in optically active form. The functionalized tetrahydrofuran derivative was synthesized via an oxocarbenium ion-mediated highly diastereoselective syn-allylation reaction. The polyene side chain was synthesized using Stille coupling reactions. Nozaki-Hiyama-Kishi coupling was utilized to construct the C-8 stereocenter and complete the synthesis of (+)-amphirionin-4.
Department of Chemistry and Department of Medicinal Chemistry, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Arun K
AK
Ghosh
Department of Chemistry and Department of Medicinal Chemistry, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
Prasanth R
PR
Nyalapatla
D008968:Molecular Conformation; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D061065:Polyketides; C000599333:amphirionin-4