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Synthesis 2017; 49(04): 755-762
DOI: 10.1055/s-0036-1588326
DOI: 10.1055/s-0036-1588326
paper
Preparation of cis-Fused Tetrahydropyranyl Lactones via Palladium-Catalysed Cyclocarbonylation of Enediols
Weitere Informationen
Publikationsverlauf
Received: 02. August 2016
Accepted after revision: 13. September 2016
Publikationsdatum:
14. Oktober 2016 (online)
![](https://www.thieme-connect.de/media/synthesis/201704/lookinside/thumbnails/ss-2016-n0550-op_10-1055_s-0036-1588326-1.jpg)
Dedicated to the memory of Kristína Csatayová
Abstract
The stereoselective palladium-catalysed cyclocarbonylation of hex-5-ene-1,4-diols affords cis-fused bicyclic lactones only. Ring-opening with N,O-dimethylhydroxylamine hydrochloride gives the corresponding Weinreb amides, and their subsequent recyclisation provides advanced synthons for the prospective synthesis of decarestrictine L. The relative configurations of all the prepared tetrahydropyrans are determined by NOESY. The attempted transformations of lactones into methyl ketones leads to an unexpected furan, the formation of which is discussed.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588326.
- Supporting Information
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For rare examples of fused tetrahydropyranyl lactones prepared by Pd-catalysed oxycarbonylation, see:
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