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

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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2017-10, Vol.139 (41), p.14392-14395
Main Authors: Line, Nathan J, Witherspoon, Brittany P, Hancock, Erin N, Brown, M. Kevin
Format: Article
Language:English
Subjects:
alkenes
Alkenes - chemistry
Cycloaddition Reaction
cycloaddition reactions
Cyclobutanes - chemistry
enantioselective synthesis
ketones
Ketones - chemistry
optical isomerism
Stereoisomerism
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Summary: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.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.7b09844