Catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters: application to 1,3-polyol/alpha-pyrone natural product synthesis.
[reaction: see text] We describe a catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of alpha,beta-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/alpha-pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.
Tosaki
Shin-Ya
SY
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Nemoto
Tetsuhiro
T
Ohshima
Takashi
T
Shibasaki
Masakatsu
M
D001685:Biological Factors / Q000138:chemical synthesis; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D006880:Hydroxy Acids / Q000138:chemical synthesis*; D011753:Pyrones / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D004952:Esters; D006880:Hydroxy Acids; D011753:Pyrones