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

Autor:	and María D. Martín-Ortega, Isabel Gràcia, Sofía Bobo, Jose Luis Chiara
Rok vydání:	1999
Předmět:	Chemistry Organic Chemistry Mannose Ether Oxazoline Ring (chemistry) Biochemistry Combinatorial chemistry Aminocyclitol chemistry.chemical_compound Intramolecular force Stereoselectivity Physical and Theoretical Chemistry Trifluoromethanesulfonate
Zdroj:	Digital.CSIC. Repositorio Institucional del CSIC instname
Popis:	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. 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. 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ae3639de67848d8bce7cb9c8c28ecb50 http://hdl.handle.net/10261/30940 Zobrazit plný text záznamu