Total synthesis of (+)-herboxidiene/GEX 1A

• DOI: 10.1039/c7ob00072c
• Publication Date: 2017-01-30T11:55:02Z
• Authors: Alejandro Gómez-P...; Miquel Pellicena; Katrina Krämer; Pedro Romea; Fèlix Urpí; Gabriel Aullón; José M. Padrón
• Keywords: Molecular Conformation; Stereoisomerism; Fatty Alcohols; 01 natural sciences; Pyrans; 0104 chemical sciences

A total synthesis of (+)-herboxidiene/GEX 1A has been accomplished from (R)- and (S)-lactate esters in a highly efficient manner. Key steps the involve substrate-controlled titanium-mediated aldol reactions chiral lactate-derived ethyl ketones, an oxa-Michael cyclization, Ireland-Claisen rearrangement, Suzuki coupling. Furthermore, computational studies reaction have unveiled dramatic influence intramolecular hydrogen bonds on stereochemical outcome such cyclizations, whereas biological analyses clearly proved important cytoxicity 1A.