Synthetic study of aquayamycin. Part 1: Synthesis of 3-(phenylsulfonyl)phthalides possessing a β-C-olivoside

Authors :: Mitsujiro Tanabe
Takashi Matsumoto
Toshiyuki Hamura
Yokusu Kuriyama
Hiroki Yamaguchi
Keisuke Suzuki
Source :: Tetrahedron Letters. 41:8383-8387
Publication Year :: 2000
Publisher :: Elsevier BV, 2000.
Abstract: An efficient synthetic route to 3-(phenylsulfonyl)phthalides possessing a β- C -olivoside was developed by exploiting the regioselective [2+2] cycloaddition of benzyne with ketene silyl acetal. The compounds are useful in the total synthesis of the angucyclines, including aquayamycin.

Subjects :: Aquayamycin
Silylation
Stereochemistry
Organic Chemistry
Acetal
Ketene
Regioselectivity
Total synthesis
Biochemistry
Aryne
Cycloaddition
chemistry.chemical_compound
chemistry
Drug Discovery

Tools