Pharmacological properties of biphenyl-neolignans, such as honokiol, magnolol, and obovatol, from Magnolia species have been reported to include anti-inflammatory, anti-allergic, anti-bacterial, and anti-depressant activities. In addition to these biphenyl-neolignans, 4-O-methylhonokiol was isolated from Magnolia species and exhibits various biological activities. Interestingly, 4-O-methylhonokiol has the higher anti-inflammatory activity than honokiol and its analogs. Moreover, 4-O-methylhonokiol was recently found to exhibit neurotropic and memory improving activity.The structural feature of 4-O-methylhonokiol is the unsymmetrical 5,3'-diallyl-biphenyl, which differs from honokiol by the methoxy group at its C4 position. In spite of its interesting biological activities, only one pioneering total synthesis of 4-O-methylhonokiol has been reported by Denton group. Because of that, we interested to develop a new and scalable synthesis of 4-O-methylhonokiol and its analogs. Therefore, we attempted to develop an efficient and shorter method for the total synthesis of 4-O-methylhonokiol featuring a Suzuki-Miyaura cross-coupling as the key step.

Efficient and scalable synthesis of 4-<i>O</i>-methylhonokiol

243rd National Meeting (2012)

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Efficient and scalable synthesis of 4-O-methylhonokiol