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Recognition of one alkoxy carbonyl group from the two in a molecule by a Lewis acid was investigated using 1a-e in the Diels-Alder reaction with diene 6. Combination of 1a and BF 3 .OEt 2 provided the highest efficiency to afford 7a, thus showing evidence for the site-selective coordination of BF 3 .OEt 2 to the MOM-oxy carbonyl group in 1a. Furthermore, the generality...
Macrosphelides C and F were synthesized by lactonization of 14-oxo seco acids at the O(10)C(11) bond followed by reduction and Mitsunobu inversion of the resulting hydroxyl group. The seco acids were prepared from the corresponding furans by furan ring-opening with NBS followed by further oxidation of the 4-oxo-2-alkenals with NaClO2.
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