Abstract
Base catalyzed reaction of active methylene compounds or oxygen catalyzed reaction of trialkylboranes via radical pathway with 5-trimethylsilyl-2-cyclohexenone (1) gave the corresponding products with modest to high (3:2– 20:1) diastereopurities. High diastereoselectivity (6:1– > 20:1) was observed in the reactions of enol silyl ethers, allylsilanes, hydrogenperoxide, and diethylaluminium cyanide with 1 and its 3-substituted derivatives. Full details of the total synthesis of (+)-ramulosin utilizing the diastereospecific product are also described.
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