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.

4 páginas, 5 esquemas.-- This work was presented in part at the 19th International Carbohydrate Symposium, San Diego, 1998.-- Supporting Information Available: Complete experimental procedures and characterization data for the new compounds in Schemes 1-5 and 1H NOE data for compound 12. This material is available free of charge via the Internet at http://pubs.acs.org.

This work was supported by Grant PB-96-0833 from DGES, Ministerio de Educación y Cultura of Spain. A predoctoral fellowship (to I.S.de G.) from Ministerio de Educación y Cultura is also gratefully acknowledged.

Peer reviewed