Enantiodivergent Chemoenzymatic Synthesis of (S)- and (R)-(Z)-9-Dodecyl-4,5,8,9-tetrahydro-3H-oxonin-2-one as Analogues of Topsentolides

Title: Enantiodivergent Chemoenzymatic Synthesis of (S)- and (R)-(Z)-9-Dodecyl-4,5,8,9-tetrahydro-3H-oxonin-2-one as Analogues of Topsentolides

Volume: 9 Issue: 3

Author(s): Isolde Wetzel, Jurgen Krauss and Franz Bracher

Affiliation:

Keywords: Cytotoxic activity, Grubbs catalyst, kinetic enzymatic resolution, lipase, ring closing metathesis, topsentolides, olefin, metathesis, Friedel-Crafts acylation, marine sponge

Abstract: (Z)-4,5,8,9-Tetrahydro-3H-oxonin-2-one is the core of naturally occurring topsentolides, cytotoxic oxylipins isolated from a marine sponge of the genus Topsentia. An enantiodivergent approach to topsentolide analogues was worked out with a lipase-catalyzed kinetic resolution of a secondary alcohol and a ring-closing metathesis giving the unsaturated nine-membered lactone as key steps.

Cite this article as:

Wetzel Isolde, Krauss Jurgen and Bracher Franz, Enantiodivergent Chemoenzymatic Synthesis of (S)- and (R)-(Z)-9-Dodecyl-4,5,8,9-tetrahydro-3H-oxonin-2-one as Analogues of Topsentolides, Letters in Organic Chemistry 2012; 9 (3) . https://dx.doi.org/10.2174/157017812800167466