Stereoselective β‐<i>C</i>‐Glycosylation by a Palladium‐Catalyzed Decarboxylative Allylation: Formal Synthesis of Aspergillide A

Jing Zeng, Jimei Ma, Shao‐Hua Xiang, Shuting Cai, Xue‐Wei Liu

Angewandte Chemie International Edition · 2013 · 86 citations · 84 references

Concepts

Abstract

Mild and sweet: The title reaction proceeds under mild conditions with high regio- and diastereoselectivity (see scheme, PG=protecting group, DiPPF=1,1′-bis(diisopropylphosphino)ferrocene). This reaction is suitable for a wide range of glycal-derived γ-ketone esters and affords C-glycosides with exclusive β-selectivity. The method was further applied to a concise formal synthesis of aspergillide A. As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

References

84