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Convergent total syntheses of (-)-Rubriflordilactone B and (-)-pseudo-Rubriflordilactone B

DOI: 10.1002/anie.201908917 DOI Help

Authors: Mujahid Mohammad (University of Oxford) , Venkaiah Chintalapudi (University of Oxford) , Jeffrey M. Carney (Christopher Newport University) , Steven J. Mansfield (University of Oxford) , Polyanna Sanderson (University of Oxford) , Kirsten E. Christensen (University of Oxford) , Edward A. Anderson (University of Oxford)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Angewandte Chemie International Edition

State: Published (Approved)
Published: October 2019
Diamond Proposal Number(s): 20876

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.

Journal Keywords: cyclotrimerization; natural products; structure elucidation; schinorterpenoids; total synthesis

Subject Areas: Chemistry

Instruments: I19-Small Molecule Single Crystal Diffraction