Stereoselective synthesis of zooxanthellactone

Partial reductions of carboxylic acids and their derivatives to aldehydes

“…In 2017, an iridium(III) metallacycle catalyst (56) was made available by Agbossou-Niedercorn and Michon's group for aldehyde synthesis by selective reduction of some carboxylic acids with hydrosilanes (Scheme 15). 50 However, the chemoselectivity for this reduction was not well controlled, and it was highly substrate-sensitive.…”

“…The most famous reduction of acyl halides to aldehydes was the Rosenmund reduction, which has found applications in the large-scale syntheses of atovaquone, an anti-pneumocystic agent, 54 and AMD070, a HIV entry inhibition candidate, 55 and zooxanthellactone, a marine natural product. 56 The classic Rosenmund reduction features a poisoning Pd catalyst and hydrogen gas, and suffers from some chemical and practical limitations. The chemical outcomes are very sensitive to the degree of catalyst poisoning and slight changes of temperature.…”

Synthesis of 5-(S)-HETE, 5-(S)-HEPE and (+)-zooxanthellactone: Three hydroxylated polyunsaturated fatty acid metabolites

“…175 This natural product has also been stereoselectively synthesized in our group. 176 Scheme 1.31 The synthesis of racemic 5-HETE (7). 171 Skattebøl and co-workers have utilized both EPA (2) and DHA (3) as starting materials in the syntheses of sulfur-and oxygen-containing fatty acids, 177 as well as three metabolites of EPA (2) and DHA (3).…”