Fig. 3: Metalation–borylation strategies utilized for the installation of stereocentres of caylobolide A. | Nature Synthesis

Fig. 3: Metalation–borylation strategies utilized for the installation of stereocentres of caylobolide A.

From: The combination of synthesis and ultra-high-resolution NMR spectroscopy reveals the correct structure of caylobolide A

Fig. 3

a, Different methods used for the generation of metalated carbenoids for application in metalation–borylation. Blue, generation of a tin-based carbenoid precursor; red, generation of an α-sulfinylbenzoate carbenoid precursor. The Δ above the top right arrow represents heat. b, Retrosynthetic analysis of caylobolide A. Following disconnection of the macrolactone, the complex polyol intermediate CF_1-4 was further disconnected into four fragments, all unified by metalation–borylation strategies. c, Strategy to install 1,5-polyols through iterative hydroboration–homologation of an alkene followed by stereospecific oxidation. d, Strategy to install 1,3-polyols through iterative diboration–homologation of an alkene followed by stereospecific oxidation. p-Tol, para-tolyl; pin, pinacolato; TES, triethylsilyl; THF, tetrahydrofuran.

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