Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: total synthesis of epiplakinic acid F.
The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared.
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, The Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.
Xiang-Yin
XY
Tian
Jian-Wei
JW
Han
Qiong
Q
Zhao
Henry N C
HN
Wong
D002625:Chemistry, Organic / Q000379:methods*; D004148:Dioxolanes / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D010545:Peroxides / Q000138:chemical synthesis* / Q000737:chemistry
D004148:Dioxolanes; D004952:Esters; D010545:Peroxides; C433591:epiplakinic acid F