title: Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.
abstract: The total synthesis of psymberin was achieved employing a readily available chiral epoxide to prepare two of the three subunits in the natural product. The key reaction was a highly stereoselective organocatalytic oxa-conjugate addition reaction of α,β-unsaturated ketone catalyzed by primary diamine for the synthesis of the 2,6-trans-tetrahydropyran embedded in psymberin.
authors: Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
authors: Seong Rim
authors: SR
authors: Byeon
authors: Heekwang
authors: H
authors: Park
authors: Hyoungsu
authors: H
authors: Kim
authors: Jiyong
authors: J
authors: Hong
mesh_terms: D002384:Catalysis; D003374:Coumarins; D003959:Diamines / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D003374:Coumarins; D003959:Diamines; D007659:Ketones; D011714:Pyrans; D011753:Pyrones; C498383:psymberin