1333318-97-0Relevant articles and documents
A unified strategy for the synthesis of (-)-maoecrystal Z, (-)-trichorabdal A, and (-)-longikaurin E
Yeoman, John T.S.,Cha, Jacob Y.,Mak, Victor W.,Reisman, Sarah E.
, p. 4070 - 4088 (2014)
Herein we describe in full our investigations that led to the completion of the first total syntheses of (-)-maoecrystal Z, (-)-trichorabdal A, and (-)-longikaurin E. The unified strategy employs a TiIII-mediated reductive epoxide coupling to rapidly prepare a key spirolactone. Highly diastereoselective SmII-mediated reductive cyclizations and a Pd II-mediated oxidative cyclization enable the construction of three architecturally distinct ent-kauranoid frameworks from this common intermediate.