Abstract
AbstractA convenient synthetic route towards structurally intriguing hyacinthacines bearing an additional hydroxymethyl substituent at the C‐5 position is described. The strategy relies on syn‐stereoselective 1,3‐dipolar cycloaddition of D‐mannose‐derived nitrone, which provides the required stereochemistry at the A‐ring and at the bridgehead C‐7a carbon atom in target pyrrolizidines. Consecutive Horner‐Wadsworth‐Emmons olefination 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 B2.
Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
