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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Total Synthesis of Immunosuppressive Mycestericin E and G Enabled by a Highly Stereoselective Nitroso-Ene Cyclization
Yao Zhao1, Yuzhen Ding2,3, Yalan Peng4
1School of Environmental and Chemical Engineering, Shanghai Institute of Technology, Shanghai 201418, PR China.
Abstract:
This report describes a streamlined synthesis of immunosuppressive mycestericin E and G through a highly stereoselective nitroso-ene cyclization in 11-12 steps using readily available materials. The stereochemical outcome in the formation of a Nα-quaternary stereogenic center is rationalized by a trajectory based on the polar diradical intermediate and subsequent hydrogen transfer. Julia olefination offers a facile chain elongation method that presents a viable strategy for structural derivatization in future medicinal applications.
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