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Brown allylation methodology has been employed to provide seven of the eight possible isomers of the (ZE)(EZ) spiroacetal system representing the CD ring fragment (C17-C28) of spongistatin 1. The stereochemistry of the isomers follows from high-field NMR examinations which furnish insights into the trends in the NMR data for these ketal structures.

Stereoselective synthesis and stereochemistry of seven isomeric spiroacetal structures based on the C17–C28 fragment (CD rings) of spongistatin 1