Asymmetric total synthesis of (-)-Linderol A |
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Authors: | Yamashita Masayuki Yadav Navnath Dnyanoba Sawaki Takeshi Takao Ikuko Kawasaki Ikuo Sugimoto Yasuko Miyatake Akemi Murai Kousuke Takahara Ayano Kurume Ai Ohta Shunsaku |
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Institution: | Department of Functional Molecular Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi-Nakauchi 5, Yamashina, Kyoto 607-8414, Japan. |
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Abstract: | The first asymmetric total synthesis of (-)-Linderol A, a potent inhibitor of melanin biosynthesis of cultured B-16 melanoma cells, has been achieved via two key reactions: a diastereoselective 2+2] photocycloaddition of a coumarin-3-carboxylate bearing a chiral auxiliary with 3-methyl-1-butene and a subsequent stereoconvergent transformation of the photoadducts with use of dimethylsulfoxonium methylide to afford a tetrahydrodibenzofuran derivative. |
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