Alkene Ozonolysis in the Presence of Diazo Functionality: Accessing an Intermediate for Squalestatin Synthesis

Abstract

Studies on both the propensity for intramolecular cycloaddition between diazo and alkene functionality, and the tolerance of α-substituted α-diazoesters towards ozone in the presence of an alkene, led to chemoselective alkene ozonolysis of an ε-unsaturated-α-diazoester to give a key racemic diazoketone for the synthesis of 6,7-dideoxysqualestatin H5.

Key words

6,7-dideoxysqualestatin H5 - squalestatin synthesis - alkene ozonolysis - intramolecular cycloaddition - diazo stability - pyrazoline

• References and Notes

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