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.
| Author details: | Bernd SchmidtORCiDGND, Oliver Kunz |
|---|---|
| DOI: | https://doi.org/10.3762/bjoc.9.289 |
| ISSN: | 1860-5397 |
| Title of parent work (English): | Beilstein journal of organic chemistry |
| Publisher: | Beilstein-Institut zur Förderung der Chemischen Wissenschaften |
| Place of publishing: | Frankfurt, Main |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2013 |
| Publication year: | 2013 |
| Release date: | 2017/03/26 |
| Tag: | dienes; enzyme catalysis; lactones; metathesis; natural products; ruthenium |
| Volume: | 9 |
| Number of pages: | 12 |
| First page: | 2544 |
| Last Page: | 2555 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG) [Schm 1095/6-2] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
| Publishing method: | Open Access |
