A convenient synthetic route towards structurally intriguing hyacinthacines bearing an additional hydroxymethyl substituent at the C-5 position is described. The strategy relies on synstereoselective 1,3-dipolar cycloaddition of D-mannose-derived nitrone, which provides the required stereochemistry at the Aring and at the bridgehead C-7a carbon atom in target pyrrolizidines. Consecutive Horner-Wadsworth-Emmons olefina-tion and intramolecular reductive amination cyclization are employed for the B-ring construction with an emphasis on the stereochemistry of the newly formed stereocenter at C-5. The simplicity of this method is exemplified by effective and highly stereocontrolled synthesis of the unnatural (-)-enantiomer of hyacinthacine B 2 .