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Stereospecific Sulfur-Mediated Cleavage of a Spirocyclobutanone: Synthesis of a Fully Functional Precursor to the CP
Dongfang Meng1, Samuel J Danishefsky1
1Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021 (USA), Fax: (+1) 212-772-8691 (and) Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027 (USA).
Abstract:
A reaction sequence made up of a Sakurai reaction, ketene cyclization, sulfur-directed Baeyer-Villiger reaction, and tandem lactone cleavage/isomerization provided the fully functionalized core of the CP compounds. Key steps were the methanolysis of 1, which leads via 2 to the CP precursor 3.
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