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

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

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 3 , 2012

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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.

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

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Article Details

VOLUME: 9
ISSUE: 3
Year: 2012
Page: [169 - 174]
Pages: 6
DOI: 10.2174/157017812800167466
Price: $58

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