Abstract:
The enantioselective synthesis of a dimeric pyranonaphthoquinone closely related to cardinalin 3 is described. Key steps include the Hauser-Kraus annulation between a cyanophthalide and a chiral enone to create the naphthalene skeleton, a Suzuki-Miyaura homocoupling of an aryl triflate to construct the biaryl bond and a double stereoselective lactol reduction to install the 1,3-cis stereo-chemistry of the pyran rings.