Abstract
The bicyclo[4.3.0]nonane (C 11–C 21) fragment of stawamycin has been prepared by a sequence involving 11 steps (10% overall yield) from methyl ( R)-(−)-3-hydroxy-2-methylpropionate. Key steps are a Pd-catalysed Stille coupling reaction between a vinyl iodide and a vinyl stannane followed by an intramolecular Diels–Alder cycloaddition reaction to give the desired adduct as the major isomer in 21% overall yield.
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