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.
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]
In combination with studies from the Li group,[9] we demonstrate that this proposed structure is the likely identity of this natural product
Summary
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. Syntheses of rubriflordilactone A were described by the Li group,[4] and by ourselves.[5] 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 (the form of the natural product characterized by X-ray crystallographic analysis) did not match that recorded for rubriflordilactone B by the Sun group.[3] This finding appeared to imply the existence of two
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