Catalytic enantioselective total synthesis of (-)-platyphyllide and its structural revision.
The catalytic asymmetric total synthesis of platyphyllide has been accomplished. A key highly substituted cyclohexene derivative has been obtained by the catalytic asymmetric Diels-Alder reaction of Danishefsky diene with an electron-deficient alkene. The Diels-Alder adduct was converted to a protected cyclohexane-1,3-dione in chiral form by catalytic Ito-Saegusa oxidation. Although the reported structure of platyphyllide was successfully synthesized, the optical rotation was opposite that of the natural compound. The absolute configuration of natural (-)-platyphyllide is revised to be a (6S,7S)-enantiomer.
Hiraoka
Shiharu
S
Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Harada
Shinji
S
Nishida
Atsushi
A
D000475:Alkenes / Q000737:chemistry; D001572:Benzofurans; D002384:Catalysis; D003510:Cyclohexanes; D053138:Cyclohexenes / Q000138:chemical synthesis* / Q000737:chemistry*; D007659:Ketones; D015394:Molecular Structure; D009904:Optical Rotation; D013237:Stereoisomerism
D000475:Alkenes; D001572:Benzofurans; D003510:Cyclohexanes; D053138:Cyclohexenes; D007659:Ketones; C551783:platyphyllide; C052568:cyclohexene; C506365:Cyclohexane