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Synlett 1991; 1991(8): 579-580
DOI: 10.1055/s-1991-21983
DOI: 10.1055/s-1991-21983
letter
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A New Stereoselective Approach to Oxygenated Carbocycles: Asymmetric Synthesis of the Cyclohexyl Fragment of FK-506
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Publication History
Publication Date:
07 March 2002 (online)
A general synthetic method for oxygenated carbocycles has been demonstrated which involves the stereocontrolled intramolecular ene reaction of oxygenated δ,ε-unsaturated aldehydes with methylaluminum bis(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR). This strategy is successfully applied to the asymmetric synthesis of the cyclohexyl fragment [(1R,3R,4R)-4-benzyloxy-3-methoxycyclohexanecarbaldehyde] of immunosuppressive FK-506.