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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Synthesis of Maoecrystal P: Application of a Strained Bicyclic Synthon
Fan Su1, Yandong Lu1, Lingran Kong1
1Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.
Abstract:
A new strategy was devised for the total synthesis of highly oxidized ent-kauranoids. A highly regio- and diastereoselective intermolecular Diels-Alder cycloaddition involving a diene embedded in a substituted bicyclo[4.1.0] skeleton was used to assemble all carbon centers but C17 of the target molecule at an early stage of the synthesis. Subsequent synthetic steps, including redox manipulations, SmI2 -mediated cyclization, and isomerization reactions, afforded the antitumor natural product maoecrystal P.
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