Total synthesis of acerogenins E, G and K, and centrolobol

The first total synthesis of the diaiylheptanoid acerogenins E and K, isolated from Acer nikoense MAXIM., is described. Formation of the 13-membered m,m-cyclophane skeleton was successfully achieved on the basis of a domino process involving a Miyaura arylborylation intramolecular Suzuki reaction. The cyclization precursor was prepared via a Wittig reaction and Claisen Schmidt condensation, which proceeded in moderate yields. The total synthesis of acerogenin G and centrolobol was also achieved from a common synthetic intermediate. (C) 2013 Elsevier Ltd. All rights reserved.