Piotr Nowak - Total synthesis of (5S)-dihydroyashabushiketol

Version 1

      Publication Details (including relevant citation   information):

    Jan Romanski, Piotr Nowak, Christian Chapuis, Janusz Jurczak (2011) Tetrahedron: Asymmetry 22 (7) p. 787-790




                    Enantiomerically pure                 (+)-(5S)-dihydroyashabushiketol                 1a was obtained by the 1,3-dipolar                 cycloaddition of a nitrile oxide, generated from                 oxime 3b, to N-acryloyl                 bornane[10,2]sultam                 (2R)-2 (67%, 85% de, then                 crystallization 81%, 99% de), followed by reduction                 with DIBAL-H to aldehyde (−)-6a                (67%), Wittig reaction to isoxazoline                 (E/Z)-7 (60%),                 and finally hydrolytic hydrogenation (62%).                


      Address (URL): http://dx.doi.org/10.1016/j.tetasy.2011.04.014