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A Method for the Late-Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A

MPS-Authors
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Sommer,  Heiko
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Hamilton,  James Y.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Fürstner,  Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Sommer, H., Hamilton, J. Y., & Fürstner, A. (2017). A Method for the Late-Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A. Angewandte Chemie International Edition, 56(22), 6161-6165. doi:10.1002/anie.201701391.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002D-8AF3-C
Abstract
Treatment of alkenylstannanes with Cu(OAc)2/Et3N affords the corresponding enol esters or ketones under conditions that proved compatible with many common functionalities; these include groups that would neither survive under the standard Tamao–Fleming conditions for the oxidation of Csp2 −SiR3 bonds nor under the conditions commonly used to oxidize C−B bonds. Chiral centers adjacent to the unveiled carbonyls are not racemized and competing protodestannation is marginal, even if the substrate carries unprotected −OH groups as internal proton sources. Therefore, the procedure is well suited for the preparation of acyloin and aldol derivatives. These enabling virtues are illustrated by a concise approach to the bicyclic lipid paecilonic acid A.