Asymmetric total synthesis of (-)-Linderol A.
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.
Yamashita
Masayuki
M
Department of Functional Molecular Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi-Nakauchi 5, Yamashina, Kyoto 607-8414, Japan.
Yadav
Navnath Dnyanoba
ND
Sawaki
Takeshi
T
Takao
Ikuko
I
Kawasaki
Ikuo
I
Sugimoto
Yasuko
Y
Miyatake
Akemi
A
Murai
Kousuke
K
Takahara
Ayano
A
Kurume
Ai
A
Ohta
Shunsaku
S
D000818:Animals; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D045744:Cell Line, Tumor; D003500:Cyclization; D008546:Melanoma, Experimental / Q000473:pathology; D051379:Mice; D013057:Spectrum Analysis / Q000379:methods; D013237:Stereoisomerism
D001572:Benzofurans; C429131:linderol A