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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Toward the Total Synthesis of Myrindole A: Assembly of Fully Functionalized Cyclohexenone
Gang Wei1, Bin Liang2, Kun-Yu Xin2
1College of Intelligent Metallurgy, Guangxi Modern Polytechnic College, Hechi 547000, China.
Abstract:
A rapid installation of the highly functionalized six-membered carbocycle-based core embedded in the central position of myrindole A was reported. Key transformations include (1) an intramolecular Diels-Alder reaction with N-substituted 2-oxazolone as the dienophile to directly introduce the structurally complex tetracyclic subunit characterized with four continuous stereocenters (one quaternary), (2) an air-promoted multifold cascade reaction to realize the formal remote C-H oxidation, and (3) an unprecedented ring contraction to finish the creation of the fully functionalized cyclohexenone nucleus via formal 1,2-trans migration of the ArO group. The possible reaction pathways for the aforementioned transformations were tentatively put forward.
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