exo-Brevicomin - O O Making A mCPBA H H O H + ,H 2 O O O H...

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exo-Brevicomin I left a carbon off some of the structures that I wrote on the board today, for which I apologize. The correct structures are shown below. O OH OH O O H 3 C +H + , cleave CO add H 2 O, -H + open1st acetal: H + , cleave CO open 2nd acetal: add H 2 O, -H + (after reorienting carbon chain) Because acetal formation is reversible, loss of H 2 O from a diastereomer of A in acid will make exo-brevicomin. O OH OH TsOH, (separate H 2 O) A O O (need to protect as an acetal or will get Baeyer- Villiger reaction in next step)
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Unformatted text preview: O O Making A mCPBA H H O H + ,H 2 O O O H OH HO H (acid cat. opening with inversion) H + ,H 2 O (separate H 2 O) (+ enantiomer) exo-brevicomin exo-brevicomin racemic I would not expect you to be able to predict which diastereomer of A was necessary HO O H 3 C HO . I would hope that you would be able to hydrolyze the two acetals to an open-chain structure (without the relative stereochemistry of the diol)....
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