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A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A.

ABSTRACT: A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed that features an 8-aminoquinolinamide directed C-H arylation reaction. The C-H arylation products were derivatized through subsequent decarboxylative coupling processes. This synthetic strategy enabled a 9-step enantioselective total synthesis of the antiproliferative meroterpenoid (+)-rumphellaone A.

SUBMITTER: Beck JC

PROVIDER: S-EPMC6385545 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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A modular approach to prepare enantioenriched cyclobutanes: synthesis of (+)-rumphellaone A.

Beck Jordan C JC Lacker Caitlin R CR Chapman Lauren M LM Reisman Sarah E SE

Chemical science 20181219 8

A modular synthesis of enantioenriched polyfunctionalized cyclobutanes was developed that features an 8-aminoquinolinamide directed C-H arylation reaction. The C-H arylation products were derivatized through subsequent decarboxylative coupling processes. This synthetic strategy enabled a 9-step enantioselective total synthesis of the antiproliferative meroterpenoid (+)-rumphellaone A. ...[more]

PMID: 30881657

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