Visible-light-mediated Barbier allylation of aldehydes and ketones via dual titanium and photoredox catalysis

This study reports a photocatalytic Barbier-type allylation of various aldehydes and ketones with allyl halides for the synthesis of homoallylic alcohols driven by dual titanium and photoredox catalysis.

Stereoselective Total Synthesis of (6S)-5,6-Dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one from L-Malic Acid

A stereoselective total synthesis of an antiproliferative and antifungal natural product, (6 S)-5,6-dihydro-6-[(2 R)-2-hydroxy-6-phenylhexyl]-2 H-pyran-2-one has been accomplished using the Barbier allylation, LiAlH4/LiI mediated syn-stereoselective reduction and olefin ring-closing metathesis (RCM) as the key steps. L-Malic acid was used as a chiral precursor for the construction of syn-1,3-diol moiety of the molecule.

Stereoselective Total Syntheses of (3R,5R)-Sonnerlactone and (3R,5S)-Sonnerlactone

A highly convergent and concise total syntheses of (3 R,5 R)-Sonnerlactone and (3 R,5 S) Sonnerlactone from a readily available L-malic acid is described. The following series of reactions such as Barbier allylation, photochemical esterification and Ring Closing Metathesis (RCM) are utilized as key steps to accomplish their syntheses.

First Stereoselective Synthesis of (6R,7R,8S)-8-Chlorogoniodiol

A stereoselective synthesis of (6R,7R,8S)-8-chlorogoniodiol has been achieved in a linear sequence of 12 steps and 19.8% overall yield from cinnamyl alcohol. The key steps include Sharpless asymmetric epoxidation, regioselective ring opening of epoxide, indium-mediated Barbier allylation, and Still–Gennari olefination.