Title |
Regio‐ and Stereoselective Homologation of 1,2‐Bis(Boronic Esters): Stereocontrolled Synthesis of 1,3‐Diols and Sch 725674
|
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Published in |
Angewandte Chemie. International Edition, October 2016
|
DOI | 10.1002/anie.201608406 |
Pubmed ID | |
Authors |
Alexander Fawcett, Dominik Nitsch, Muhammad Ali, Joseph M. Bateman, Eddie L. Myers, Varinder K. Aggarwal |
Abstract |
1,2-Bis(boronic esters), derived from the enantioselective diboration of terminal alkenes, can be selectively homologated at the primary boronic ester by using enantioenriched primary/secondary lithiated carbamates or benzoates to give 1,3-bis(boronic esters), which can be subsequently oxidized to the corresponding secondary-secondary and secondary-tertiary 1,3-diols with full stereocontrol. The transformation was applied to a concise total synthesis of the 14-membered macrolactone, Sch 725674. The nine-step synthetic route also features a novel desymmetrizing enantioselective diboration of a divinyl carbinol derivative and high-yielding late-stage cross-metathesis and Yamaguchi macrolactonization reactions. |
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Unknown | 1 | 50% |
Demographic breakdown
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Scientists | 2 | 100% |
Mendeley readers
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Researcher | 10 | 17% |
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