A Concise and Highly Efficient Synthesis of Trehazolin and Trehalamine Starting from d-Mannose

Autor: Gracia, I. Storch de, Bobo, S., Martin-Ortega, M. D., Chiara, J. L.
Zdroj: Organic Letters; December 1999, Vol. 1 Issue: 11 p1705-1708, 4p
Abstrakt: 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.
Databáze: Supplemental Index