Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C–H Arylation

A strategy for the construction of unsymmetrical cyclobutanes using C–H functionalization logic is demonstrated in the total synthesis of piperarborenine B and piperarborenine D (reported structure). These syntheses feature a new preparation of cis-cyclobutane dicarboxylates from commercially availa...

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Published inJournal of the American Chemical Society Vol. 133; no. 47; pp. 19076 - 19079
Main Authors Gutekunst, Will R, Baran, Phil S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.11.2011
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Cyclobutanes - chemistry
Molecular Structure
Physical Sciences
Piperidones - chemical synthesis
Piperidones - chemistry
Science & Technology
Stereoisomerism
FUNCTIONALIZATION
CYCLOPROPANE
CYCLOADDITION
(-)-INCARVILLINE
ACID
RHODIUM
BONDS
PHOTOCHEMICAL-REACTIONS
SP
CARBON-HYDROGEN
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Summary:A strategy for the construction of unsymmetrical cyclobutanes using C–H functionalization logic is demonstrated in the total synthesis of piperarborenine B and piperarborenine D (reported structure). These syntheses feature a new preparation of cis-cyclobutane dicarboxylates from commercially available coumalate starting materials and a divergent approach to the controlled cis or trans installation of the two distinct aryl rings found in the natural products using the first example of cyclobutane C–H arylation. The structure of piperarborenine D is reassigned to a head-to-head dimer, which was synthesized using an intramolecular [2+2] photocycloaddition strategy.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja209205x