A formal synthesis of psymberin.
A formal synthesis of psymberin (irciniastatin A) is presented. Notable features of the synthesis include the chemo-, regio-, and stereoselective oxidation of a 1,3-disubstituted allene, a configuration-dependent spirodiepoxide opening, the efficient syntheses of functionalized trans-2,6-disubstituted pyrans, and the union of a highly functionalized aldehyde with a pentasubstituted aryl homoenolate to give a dihydroisocumarin. [structure: see text]
Shangguan
Ning
N
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
Kiren
Sezgin
S
Williams
Lawrence J
LJ
D000447:Aldehydes / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins; D004852:Epoxy Compounds / Q000737:chemistry; D049934:Isocoumarins / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011714:Pyrans / Q000138:chemical synthesis*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D000466:Alkadienes; D003374:Coumarins; D004852:Epoxy Compounds; D049934:Isocoumarins; D011714:Pyrans; D011753:Pyrones; C498383:psymberin; C025947:propadiene