Total Synthesis of Neodysiherbaine A via 1,3-Dipolar Cycloaddition of a Chiral Nitrone Template.

Toshihiro HiraiKohki ShibataYohei NiwanoMasao ShiozakiYoshimitsu HashimotoNobuyoshi MoritaShintaro BanOsamu Tamura

Published in: Organic letters (2017)

The total synthesis of neodysiherbaine A was achieved via 1,3-dipolar cycloaddition of a chiral nitrone template with a sugar-derived allyl alcohol in the presence of MgBr2·OEt2. This cycloaddition constructed the C2 and C4 asymmetric centers in a single step. Then reductive cleavage, intramolecular SN2 reaction of the tertiary alcohol, and oxidation of the primary alcohol afforded neodysiherbaine A.

Keyphrases

alcohol consumption
molecularly imprinted
ionic liquid
capillary electrophoresis
wastewater treatment
hydrogen peroxide
dna binding