Convergent synthesis of the polyene macrolide (-)-roxaticin

SD Rychnovsky, RC Hoye

Index: Rychnovsky, Scott D.; Hoye, Rebecca C. Journal of the American Chemical Society, 1994 , vol. 116, # 5 p. 1753 - 1765

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Citation Number: 104

Abstract

Abstract:(-)-Roxaticin hasbeen synthesized frompolyol tetraacetonide5, which wasprepared by a threefold convergent route. Each of the optically pure building blocks (2.3, and 4) was prepared using a Noyori asymmetric hydrogenation. Sequential alkylation of dibromide 3 with cyanohydrin acetonides 2 and 4 followed by stereoselective reductive decyanation gave tetraacetonide 5. The initial approach to roxaticin using a I-methylcyclopropyl ether ...