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4). providing a separable mixture of C16 isomers favoring the Cram chelation product 10.
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7 methylene hydrogens as indicated below.
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Alternative protection schemes led to sulfone elimination yielding the (E)-unsaturated aldehyde, thus thwarting lactol formation. Unfortunately the TES ether did not withstand conditions leading to 25.
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Since our studies had previously led to isomers 9 and 10, which were not readily distinguished from reported data for the natural product, we are particularly grateful to Professor Gerhard Höfle (GBF, Braunschweig, Germany) for generously assisting these efforts by providing a pure sample of (+)-ratjadone for our direct comparisons.
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