A concise and highly efficient synthesis of trehazolin and trehalamine starting from D-mannose

Article abstract of DOI:10.1021/ol990904t

(formula presented) A concise synthesis of trehazolin, its aglycon, trehalamine, and a known analogue has been developed starting from D-mannose. This new approach features a very stereoselective and high-yielding ketone-oxime ether reductive carbocyclization promoted by samarium diiodide as a key step for the preparation of the aminocyclitol component and a mild and very efficient intramolecular triflate displacement reaction for the construction of the oxazoline ring.