American Chemical Society
ol062621o_si_003.cif (13.32 kB)

trans-Acetonide Controlled endo-Selective Intramolecular Nitrone−Alkene Cycloaddition of Hept-6-enoses:  A Facile Entry to Calystegines, Tropanes, and Hydroxylated Aminocycloheptanes

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posted on 2007-01-18, 00:00 authored by Tony K. M. Shing, Wai F. Wong, Taketo Ikeno, Tohru Yamada
High-yielding endo-selective intramolecular nitrone−alkene cycloaddition (INAC) reactions of hept-6-enoses controlled by a trans-acetonide to give bridged bicyclo[4.2.1]isoxazolidines exclusively are realized for the first time. The cycloadducts were readily transformed into calystegine, tropane, and hydroxylated aminocycloheptane frameworks.