title: Nitroso-dienophile additions to dendralenes: a short synthesis of branched aminosugars.
abstract: 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.
authors.affiliation: Australian Research Council Centre of Excellence for Free Radical Chemistry and Biotechnology, Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
authors.forename: Ruomeng
authors.initials: R
authors.lastname: Wang
authors.forename: Gomotsang
authors.initials: G
authors.lastname: Bojase
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
authors.forename: Michael N
authors.initials: MN
authors.lastname: Paddon-Row
authors.forename: Michael S
authors.initials: MS
authors.lastname: Sherburn