Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

Abstract

A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

DOI: 10.1021/ol901755a

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Cite this paper

@article{Ghosh2009ModelingAM, title={Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.}, author={Partha Ghosh and Yue Zhang and Thomas J. Emge and Lawrence J. Williams}, journal={Organic letters}, year={2009}, volume={11 19}, pages={4402-5} }