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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthetic studies on (+)-ophiobolin A: asymmetric synthesis of the spirocyclic CD-ring moiety
Naoyoshi Noguchi1, Masahisa Nakada
1Department of Chemistry, Faculty of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo, Japan.
Abstract:
[reaction; see text] Asymmetric synthesis of the spirocyclic CD-ring moiety of (+)-ophiobolin A is described. Fragment A, which was prepared via pig liver esterase (PLE)-mediated kinetic resolution, and fragment B, which was prepared via diastereoselective allylation and subsequent kinetic iodolactonization, were coupled to afford the allylsilane 2, which was successfully cyclized to the desired spirocyclic CD-ring moiety 1a in the presence of a Lewis acid.
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