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Convergent Total Syntheses of (-)-Rubriflordilactone?B and (-)-pseudo-Rubriflordilactone?B.

ABSTRACT: A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone?B, and the proposed structure of (-)-pseudo-rubriflordilactone?B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo-rubriflordilactone?B and provides a robust platform for further synthetic and biological investigations.

SUBMITTER: Mohammad M

PROVIDER: S-EPMC6973266 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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Convergent Total Syntheses of (-)-Rubriflordilactone B and (-)-pseudo-Rubriflordilactone B.

Mohammad Mujahid M Chintalapudi Venkaiah V Carney Jeffrey M JM Mansfield Steven J SJ Sanderson Pollyanna P Christensen Kirsten E KE Anderson Edward A EA

Angewandte Chemie (International ed. in English) 20191031 50

A highly convergent strategy for the synthesis of the natural product (-)-rubriflordilactone B, and the proposed structure of (-)-pseudo-rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium-catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the ident ...[more]

PMID: 31595605

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