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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
First stereoselective total synthesis of FD-594 aglycon
Ritsuki Masuo1, Ken Ohmori, Lukas Hintermann
1Department of Chemistry, Tokyo Institute of Technology, SORST-JST Agency, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan.
Abstract:
Stereocontrolled access to the hexacyclic core of FD-594 has been achieved. The key steps include the intramolecular S(N)Ar reaction for construction of the densely functionalized xanthone skeleton, the stereoselective lactone cleavage using a chiral nucleophile to induce the axial stereochemistry, and the SmI(2)-mediated pinacol cyclization for the stereocontrolled conversion of axially chiral biaryl dialdehyde into the corresponding trans diol.
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