Development of an approach to the synthesis of the ABC ring system of Hemibrevetoxin B |
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Authors: | Crawford Claire Nelson Adam Patel Ian |
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Institution: | School of Chemistry, University of Leeds, Leeds LS2 9JT, UK. |
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Abstract: | An efficient approach for the synthesis of a model of the ABC ring system of Hemibrevetoxin B is described. Key features include a ring expansion to yield the ring C oxepane, the reduction of a 2-furyl ketone with high levels of 1,3-stereocontrol, and an Achmatowicz oxidative ring expansion to yield the ring A tetrahydropyran. All seven stereogenic centers present in the model compound were controlled with high levels (>98:<2) of diastereoselectivity. |
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