Tetrahedron

Total synthesis of taxane terpenes: cyclase phase

Y Ishihara, A Mendoza, PS Baran

Index: Ishihara, Yoshihiro; Mendoza, Abraham; Baran, Phil S. Tetrahedron, 2013 , vol. 69, # 27-28 p. 5685 - 5701

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Citation Number: 17

Abstract

A full account of synthetic efforts toward a lowly oxidized taxane framework is presented. A non-natural taxane, dubbed 'taxadienone', was synthesized as our first entry into the taxane family of diterpenes. The final synthetic sequence illustrates a seven-step, gram-scale, and enantioselective route to this tricyclic compound in 18% overall yield. This product was then modified further to give (+)-taxadiene, the lowest oxidized member of the taxane family of ...

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