Stereoselective synthesis of the ABCD ring framework of azaspiracids

Autor:	A. C. Kunwar, Samit Kumar Dutta, Sipak Joyasawal, Jhillu S. Yadav
Rok vydání:	2007
Předmět:	Diketone Tandem Stereochemistry Organic Chemistry Ring (chemistry) Biochemistry Radical cyclization chemistry.chemical_compound chemistry Drug Discovery Stereoselectivity Sharpless asymmetric dihydroxylation Tetrahydrofuran Derivative (chemistry)
Zdroj:	Tetrahedron Letters. 48:5335-5340
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2007.05.021
Popis:	A stereoselective synthesis of the ABCD ring framework of azaspiracid-1 and azaspiracid-3 has been achieved using a tandem bis-spiroketalization protocol in the presence of a mild proton source from 1,4-diketone precursor. A tetrahydrofuran intermediate with the correct stereochemistry for the D ring of azaspiracids-1 and 3 was then taken through a linear sequence of reactions to afford the desired diketone precursor. The D-ring of azaspiracid-1 was then constructed by employing a Sharpless asymmetric dihydroxylation followed by etherification using a homoallyl derivative. The structure of the ABCD ring framework with four contiguous rings was established by extensive NMR analysis.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::98808f38b41be7e1e4e7e7afa07868ca https://doi.org/10.1016/j.tetlet.2007.05.021 Zobrazit plný text záznamu Full Text from ScienceDirect