Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 35, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202205816
Keywords
Boronic Esters; Natural Products; Ring Contraction; Stereocontrol; Stereodivergent
Categories
Funding
- EPSRC
- University of Bristol
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This study reported the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters via electrophile-induced ring contractive 1,2-metallate rearrangement, with diastereodivergent construction achieved by simple variation of the reaction solvent. The utility of this methodology was demonstrated in the asymmetric total synthesis of (+)-herbertene-1,14-diol.
The synthesis of molecules bearing two or more contiguous, quaternary stereocenters is challenging, owing to the difficulty in controlling stereochemistry whilst simultaneously constructing a sterically congested motif. Herein, we report the electrophile-induced ring contractive 1,2-metallate rearrangement of 6-membered cyclic alkenyl boronate complexes for the synthesis of cyclopentyl boronic esters bearing two contiguous, fully substituted stereocenters with high levels of stereocontrol. Remarkably, simple variation of the reaction solvent enabled their diastereodivergent construction with facile access to complementary diastereomeric pairs. The utility of our methodology is demonstrated in the asymmetric total synthesis of (+)-herbertene-1,14-diol.
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