Bioinspired enantioselective total syntheses of antibacterial callistrilones enabled by double S_N2′ cascade

Abstract

A bioinspired, catalytic approach to the enantioselective total syntheses of antibacterial callistrilones A, C-E and 13-epi-callistrilone E natural products containing unprecedented, sterically compact [1]benzofuro-[2,3-a]xanthene 6/6/6/5/6/3-fused hexacyclic skeleton is described. The...

A New Stereoselective Approach to the Substitution of Allyl Hydroxy Group in para-Mentha-1,2-diol in the Search for New Antiparkinsonian Agents

“…In this work, we showed that the interaction between chlorohydrin 7 and NaH in dioxane made it possible to synthesize epoxide (1S,5S,6R)-4 with a preparative yield of 63% (Figure 4). Dethe D. H. et al [34] also synthesized an epimeric epoxide (1S,5R,6R)-4 by treating mesylate 5 with NaH in THF. The NMR spectra of (1S,5R,6R)-4 and (1S,5S,6R)-4 are quite different and thus easily distinguishable.…”