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

共 50 条

[31] Asymmetric total synthesis of (+)-fostriecin
Reddy, YK
Falck, JR
ORGANIC LETTERS, 2002, 4 (06) : 969 - 971
[32] Asymmetric Total Synthesis of Taxol
Sun, Dongyu
Ding, Hanfeng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (12) : 4827 - 4829
[33] Asymmetric Total Synthesis of (-)-Awajanomycin
Fu, Rui
Chen, Jie
Guo, Lu-Chuan
Ye, Jian-Liang
Ruan, Yuan-Ping
Huang, Pei-Qiang
ORGANIC LETTERS, 2009, 11 (22) : 5242 - 5245
[34] ASYMMETRIC TOTAL SYNTHESIS OF (-)-PODOPHYLLOTOXIN
ANDREWS, RC
TEAGUE, SJ
MEYERS, AI
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) : 7854 - 7858
[35] Asymmetric total synthesis of Taxol®
Mukaiyama, T
Shiina, I
Iwadare, H
Saitoh, M
Nishimura, T
Ohkawa, N
Sakoh, H
Nishimura, K
Tani, Y
Hasegawa, M
Yamada, K
Saitoh, K
CHEMISTRY-A EUROPEAN JOURNAL, 1999, 5 (01) : 121 - 161
[36] Asymmetric Total Synthesis of Pedrolide
Si Ruiqi
Li Pengfei
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (03) : 1031 - 1032
[37] Asymmetric total synthesis of (+)-swainsonine
Chooprayoon, Soontorn
Kuhakarn, Chutima
Tuchinda, Patoomratana
Reutrakul, Vichai
Pohmakotr, Manat
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (02) : 531 - 537
[38] Asymmetric total synthesis of (-)-mycothiazole
Sugiyama, H
Yokokawa, F
Shioiri, T
ORGANIC LETTERS, 2000, 2 (14) : 2149 - 2152
[39] Asymmetric Total Synthesis of Phomarol
Fan, Jian-Hong
Wang, Jing-Jing
Li, Fangfang
Wang, Guannan
Guo, Qiang
Chung, Lung Wa
Li, Chuang-Chuang
CCS CHEMISTRY, 2021, 3 (12): : 348 - 357
[40] Asymmetric Total Synthesis of Cephanolide A
Zhang, Hongyuan
He, Haibing
Gao, Shuanhu
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (46) : 20417 - 20422

← 1 2 3 4 5 →