Synthesis of dl-standishinal and its related compounds for the studies on structure–activity relationship of inhibitory activity against aromatase

…, T Kajimoto, M Node, R Tanaka, M Nishizawa…

Index: Katoh, Takahiro; Akagi, Taichi; Noguchi, Chie; Kajimoto, Tetsuya; Node, Manabu; Tanaka, Reiko; Nishizawa (nee Iwamoto), Manabu; Ohtsu, Hironori; Suzuki, Noriyuki; Saito, Koichi Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 7 p. 2736 - 2748

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Citation Number: 41

Abstract

dl-Standishinal (1), an aromatase inhibitor isolated from Thuja standishii, was synthesized in 15 steps from p-formylanisole via aldol reaction of 12-hydroxy-6, 7-secoabieta-8, 11, 13-trien- 6, 7-dial (2). In the present study, we found that the aldol condensation of 2 proceeded in excellent yield with the protonic catalyst such as d-camphorsulfonic acid in CH2Cl2. Moreover, structure-activity relationship of 1 and its related compounds was studied and it ...