- Reaction of diazodiketoester 4 with methyl glyoxylate in toluene in the presence of catalytic rhodium(II) acetate generates the 6,8- dioxabicyclo[3.2.1]octane 5 as a single regio- and stereo-isomer in good yield. Elaboration provides a suitable alcohol 7 for acid-catalysed rearrangement to give the 2,8-dioxabicyclo-[3.2.1]octane skeleton 8 of the squalestatins.
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A cycloaddition-rearrangement approach to the squalestatins
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