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It is interesting that the difference of the C12 position between hydroxy alkenes 2 and 19 affected the apparent diastereoselectivity of their respective bromoetherifications. However, we notice that the net yield of tricyclic compound 15 was 70% from hydroxy alkene 2, which is comparable to that of tricyclic compound 37 (69% yield from hydroxy alkene 19). Although the reason for this result is not clear, we speculate that the undesired mode of cyclization (i.e., Figure 2, TS-B) of 19 would result in decomposition of the substrate. Similarly, bromoetherification/reduction of hydroxy alkene 48 proceeded with a seemingly better diastereoselectivity (dr = 3.5:1) than that of hydroxy alkene 63 (dr = 2:1), but the net yield of the desired tricyclic compound 49 (47%) was almost the same as that of 65 (49%) (vide infra)
-
It is interesting that the difference of the C12 position between hydroxy alkenes 2 and 19 affected the apparent diastereoselectivity of their respective bromoetherifications. However, we notice that the net yield of tricyclic compound 15 was 70% from hydroxy alkene 2, which is comparable to that of tricyclic compound 37 (69% yield from hydroxy alkene 19). Although the reason for this result is not clear, we speculate that the undesired mode of cyclization (i.e., Figure 2, TS-B) of 19 would result in decomposition of the substrate. Similarly, bromoetherification/reduction of hydroxy alkene 48 proceeded with a seemingly better diastereoselectivity (dr = 3.5:1) than that of hydroxy alkene 63 (dr = 2:1), but the net yield of the desired tricyclic compound 49 (47%) was almost the same as that of 65 (49%) (vide infra).
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47
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66249141580
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5N. See the Supporting Information for details
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5N. See the Supporting Information for details.
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