Abstract
AbstractA 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.
Highlights
A highly convergent strategy for the synthesis of the natural product (À)-rubriflordilactone B, and the proposed structure of (À)-pseudo-rubriflordilactone B, is described
The subsequent completion of rubriflordilactone B (1, Scheme 1) by Li et al.[6,7] revealed a structural ambiguity: the NMR spectroscopic data of synthetic 1 did not match that recorded for rubriflordilactone B by the Sun group.[3]
This finding appeared to imply the existence of two rubriflordilactone B natural products—one corresponding to the X-ray structure, and the other to the NMR spectroscopic data
Summary
International Edition: DOI: 10.1002/anie.201908917 German Edition: DOI: 10.1002/ange.201908917 Convergent Total Syntheses of (À)-Rubriflordilactone B and (À)-pseudo-Rubriflordilactone B Mujahid Mohammad, Venkaiah Chintalapudi, Jeffrey M. Carney, Steven J. Mansfield, Pollyanna Sanderson, Kirsten E. Christensen, and Edward A. Anderson*
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