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note
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Vicinal protons on substituted THF rings often do give rise to nOe's regardless of their relative geometries. Therefore, the presence of a strong nOe between H13 and H14 does not conclusively establish the cis configuration of substituents at C13 and C14. However, stereochemistry at C13/C14 arises from the SAD reaction of a trans-olefin, which must yield a trans-epoxide. Although it is very unlikely that the undesired diastereomer is obtained during the asymmetric epoxidation, to allow for that possibility, the relationship between H16 and H13 would have to be necessarily cis after cyclization to the tetrahydrofuran ring (note that the retention of stereochemistry during the cyclization reaction has been clearly demonstrated in ref 20). Because the trans stereochemistry is clearly established between H13 and H16, the assigned and expected cis relationship between H13 and H14 is further supported.
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