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Bidirectional cross metathesis and ring-closing metathesis/ring opening of a C-2-symmetric building block: a strategy for the synthesis of decanolide natural products

  • Starting from the conveniently available ex-chiral pool building block (R,R)-hexa-1,5-diene-3,4-diol, the ten-membered ring lactones stagonolide E and curvulide A were synthesized using a bidirectional olefin-metathesis functionalization of the terminal double bonds. Key steps are (i) a site-selective cross metathesis, (ii) a highly diastereoselective extended tethered RCM to furnish a (Z,E)-configured dienyl carboxylic acid and (iii) a Ru-lipase-catalyzed dynamic kinetic resolution to establish the desired configuration at C9. Ring closure was accomplished by macrolactonization. Curvulide A was synthesized from stagonolide E through Sharpless epoxidation.

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Author:Bernd SchmidtORCiDGND, Oliver Kunz
ISSN:1860-5397 (print)
Parent Title (English):Beilstein journal of organic chemistry
Publisher:Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Place of publication:Frankfurt, Main
Document Type:Article
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:dienes; enzyme catalysis; lactones; metathesis; natural products; ruthenium
First Page:2544
Last Page:2555
Funder:Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-2]
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
Publication Way:Open Access