Asymmetric total synthesis of (-)-Linderol A

被引：22

作者：

Yamashita, Masayuki ^{[1
]}

Yadav, Navnath Dnyanoba ^{[1
]}

Sawaki, Takeshi ^{[1
]}

Takao, Ikuko ^{[1
]}

Kawasaki, Ikuo ^{[1
]}

Sugimoto, Yasuko ^{[1
]}

Miyatake, Akemi ^{[1
]}

Murai, Kousuke ^{[1
]}

Takahara, Ayano ^{[1
]}

Kurume, Ai ^{[1
]}

Ohta, Shunsaku ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Dept Funct Mol Chem, COE Program 21, Kyoto 6078414, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

POTENT INHIBITORY-ACTIVITY; FRIEDEL-CRAFTS ACYLATION; LINDERA-UMBELLATA BARK; B-16; MELANOMA-CELLS; 2-SUBSTITUTED CYCLOPENTA<B>BENZOFURAN-3-OL DERIVATIVES; TRICYCLIC HEXAHYDRODIBENZOFURAN CONSTITUENT; DIASTEREOSELECTIVE 2+2 PHOTOCYCLOADDITION; 3-SUBSTITUTED COUMARINS; CHIRAL CYCLOHEXENONECARBOXYLATES; STEREOCONVERGENT TRANSFORMATION;

D O I：

10.1021/jo070682+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5697 / 5703

页数：7

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