This work was supported by the NRF grant funded by the Korea government (MSIP) (No. 2007-0056817), the Oxford University Press John Fell fund, and the Royal Society (RG110617).
Asymmetric Total Synthesis of (+)-Bermudenynol, a C15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation†
Article first published online: 13 NOV 2013
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 126, Issue 1, pages 276–280, January 3, 2014
How to Cite
Kim, G., Sohn, T.-i., Kim, D. and Paton, R. S. (2014), Asymmetric Total Synthesis of (+)-Bermudenynol, a C15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton, through Intramolecular Amide Enolate Alkylation. Angew. Chem., 126: 276–280. doi: 10.1002/ange.201308077
- Issue published online: 23 DEC 2013
- Article first published online: 13 NOV 2013
- Manuscript Received: 14 SEP 2013
- Korea government. Grant Number: 2007-0056817
- Oxford University Press John Fell fund
- Royal Society. Grant Number: RG110617
- Intramolekulare Amidenolat-Alkylierung;
A substrate-controlled asymmetric total synthesis of (+)-bermudenynol, a compact and synthetically challenging C15 Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This result showcases the broad utility of the IAEA methodology as a useful alternative for cases in which the ring-closing metathesis is inefficient.