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Barthel A, Kaden F, Jäger A, et al. Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis. Org Lett. 2016;18(13):3298-301doi: 10.1021/acs.orglett.6b01619.
Barthel, A., Kaden, F., Jäger, A., & Metz, P. (2016). Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis. Organic letters, 18(13), 3298-301. https://doi.org/10.1021/acs.orglett.6b01619
Barthel, André, et al. "Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis." Organic letters vol. 18,13 (2016): 3298-301. doi: https://doi.org/10.1021/acs.orglett.6b01619
Barthel A, Kaden F, Jäger A, Metz P. Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis. Org Lett. 2016 Jul 01;18(13):3298-301. doi: 10.1021/acs.orglett.6b01619. Epub 2016 Jun 22. PMID: 27333451.
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Org Lett. 2016 Jul 01;18(13):3298-301. doi: 10.1021/acs.orglett.6b01619. Epub 2016 Jun 22.

Enantioselective Synthesis of Guaianolides in the Osmitopsin Family by Domino Metathesis.

Organic letters

André Barthel, Felix Kaden, Anne Jäger, Peter Metz

Affiliations

  1. Fachrichtung Chemie und Lebensmittelchemie, Organische Chemie I, Technische Universität Dresden , Bergstrasse 66, 01069 Dresden, Germany.

PMID: 27333451 DOI: 10.1021/acs.orglett.6b01619

Abstract

Relay metathesis enabled an improved access from (S)-citronellal to the marine trisnorguaiane (-)-clavukerin A. This hydroazulene was applied as an advantageously functionalized building block for the asymmetric synthesis of the sesquiterpene lactone osmitopsin and the proposed structure of 4,5-epoxyosmitopsin using a chemo-, regio-, and diastereoselective diepoxide opening as the key step.

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