Synthesis of (+/-)-epi-stegobinone utilizing silacyclopropanes as synthetic intermediates.
The synthesis of (+/-)-1'-epi-stegobinone has been accomplished in ten steps and 17% overall yield from a recently reported silacyclopropane-derived diol. All stereocenters of the final product were established relative to the stereochemistry of the initial silacyclopropane. This synthesis represents the first time silacyclopropane reactivity has been employed in a target-directed synthesis.
Calad
Stacie A
SA
Department of Chemistry, University of California, Irvine, California 92697-2025, USA.
Ciraković
Jelena
J
Woerpel
K A
KA
D003500:Cyclization; D003521:Cyclopropanes / Q000737:chemistry*; D008956:Models, Chemical; D011753:Pyrones / Q000138:chemical synthesis*; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
D003521:Cyclopropanes; D011753:Pyrones; C101374:stegobinone; D012825:Silicon