AI Article Synopsis

  • The report outlines an efficient method for synthesizing mycestericin E and G, focusing on a specific reaction called nitroso-ene cyclization that uses common materials and involves 11-12 steps.
  • It explains how the formation of a specific type of stereochemical center is guided by a polar diradical intermediate, which aids in understanding the reaction's outcome.
  • The authors highlight the use of Julia olefination as a simple technique for extending the molecular chain, suggesting its potential for creating derivatives applicable in medicine.

Article 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 α-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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http://dx.doi.org/10.1021/acs.orglett.3c01082DOI Listing

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