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A formal synthesis of psymberin
Ning Shangguan1, Sezgin Kiren, Lawrence J Williams
1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA.
Abstract:
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]
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