Reduction of heterocyclic-derived aldol adducts 2 and 3 using NaBH(OAc)3 is stereoselective and proceeds via a hydroxy-directed mechanism to give 6 and 7, respectively, thereby complementing the stereoselectivity available with NaBH4; a synthesis of (+)-8,8a-diepicastanospermine 11 from diol 6 is described.
S. H. J. Thompson, R. S. Subramanian, J. K. Roberts, M. S. Hadley and T. Gallagher, J. Chem. Soc., Chem. Commun., 1994, 933 DOI: 10.1039/C39940000933
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