- Asymmetric total synthesis of (-)-Linderol A.
Asymmetric total synthesis of (-)-Linderol A.
The Journal of organic chemistry (2007-06-21)
Masayuki Yamashita, Navnath Dnyanoba Yadav, Takeshi Sawaki, Ikuko Takao, Ikuo Kawasaki, Yasuko Sugimoto, Akemi Miyatake, Kousuke Murai, Ayano Takahara, Ai Kurume, Shunsaku Ohta
PMID17579456
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.
MATERIALS