Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.

Autor:	Line NJ; Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States., Witherspoon BP; Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States., Hancock EN; Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States., Brown MK; Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States.
Jazyk:	angličtina
Zdroj:	Journal of the American Chemical Society [J Am Chem Soc] 2017 Oct 18; Vol. 139 (41), pp. 14392-14395. Date of Electronic Publication: 2017 Oct 06.
DOI:	10.1021/jacs.7b09844
Abstrakt:	An enantioselective synthesis of ent-[3]-ladderanol is presented. The ladderanes are an interesting class of molecules for their unique structure of fused cyclobutane rings as well as their perceived biological function of organism protection. The route hinges on the development and application of a chirality transfer [2+2] cycloaddition of an allenic ketone and alkene. Further stereocontrolled transformations allowed for completion of the synthesis. The scope of the chirality transfer [2+2] cycloaddition is also presented.
Databáze:	MEDLINE
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