Stereoselective Synthesis of a Monocyclic Peloruside A Analogue

DOI: 10.1021/ol401103p. Publication Date (Web): May 8, 2013. Copyright © 2013 American Chemical Society. Cite this:Org. Lett. 15, 10, 2570-2570. Page...
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ORGANIC LETTERS 2013 Vol. 15, No. 10 2570–2570

Additions and Corrections Volume 12, 2010

Christoph W. Wullschleger, J€urg Gertsch, and Karl-Heinz Altmann* Stereoselective Synthesis of a Monocyclic Peloruside A Analogue Page 1122. In Scheme 6, the reaction of metalated vinyl iodide 7 with aldehyde 8 was reported to produce a 2/1 mixture of 5 and its 13R diastereoisomer. This is not correct; in fact, the reaction gave the desired 13S isomer 5 selectively. Rather than the 13R isomer of 5, the inseparable side product obtained in the reaction was ketone 5-SP. A corrected reaction scheme is shown below.

Thus, while the subsequent oxidation/reduction sequence enabled the removal of 5-SP, it would not have been required to produce 5 as a single stereoisomer. 10.1021/ol401103p Published on Web 05/08/2013