Metathesis Reactions in Domino Processes

Enantioselective Total Synthesis of the Guaianolide (−)-Dehydrocostus Lactone by Enediyne Metathesis

“…Due to our interest in the synthesis of hydroazulene natural products by domino metathesis, we developed a new approach to (−)-dehydrocostus lactone ( 1 ) by an enediyne strategy. Noteworthy, there are only a few examples for domino metathesis reactions with substrates bearing more than one triple bond. , As depicted in Scheme , our synthesis was based on the disassembly of guaianolide 1 to a hydroazulene core structure, which should allow facile functionalization in the desired stereochemical fashion. We assumed triene 9 to be a suitable intermediate that might undergo exhaustive hydroboration/oxidation to give triol 10 in a substrate-induced diastereoselective manner.…”