Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars.

Wang, Ruomeng; Bojase, Gomotsang; Willis, Anthony C; Paddon-Row, Michael N; Sherburn, Michael S

Wang, Ruomeng; Bojase, Gomotsang; Willis, Anthony C; Paddon-Row, Michael N; Sherburn, Michael S.

Afiliación

Wang R; Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.

Org Lett ; 14(22): 5652-5, 2012 Nov 16.

Article en En | MEDLINE | ID: mdl-23106239

RESUMEN

The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.

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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2012 Tipo del documento: Article País de afiliación: Australia Pais de publicación: Estados Unidos

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