The intramolecular oxa-Michael reaction for tetrahydropyran formation : mechanism and synthesis

Content Provider	Semantic Scholar
Author	Csókás, Dániel
Copyright Year	2019
Abstract	Despite the vast amount of precedents of the stereoselective oxa-Michael cyclisation for THP formation, no clear explanation for the origin of stereocontrol has been disclosed. Thus, we intend to provide a tangible explanation for the observed selectivity, which is based on a combined DFT and experimental study. The ambiguous structural elucidation and the insufficient NMR data of Cryptoconcatone H prompted us to embark on a synthesis of the reported structure. The cis-THP core of the proposed structure was established via a tandem deprotection-intramolecular oxa-Michael cyclisation. Our synthetic study provides evidence that the proposed structure of the isolated natural product is incorrect.
File Format	PDF HTM / HTML
DOI	10.32657/10220/48088
Alternate Webpage(s)	https://spms.ntu.edu.sg/ChemistryandBiologicalChemistry/Oral-Defense/Documents/2018/Oral%20Defence%20Detailed%20Poster%20Csokas%20Daniel.pdf
Alternate Webpage(s)	https://doi.org/10.32657/10220%2F48088
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article