Asymmetric Allylboration of <i>vic</i>‐Tricarbonyl Compounds: Total Synthesis of (+)‐Awajanomycin

Malte Wohlfahrt, Klaus Harms, Ulrich Koert

Angewandte Chemie International Edition · 2011 · 27 citations · 13 references

Concepts

Abstract

To the core: An efficient total synthesis of (+)-awajanomycin was achieved starting with an asymmetric allylboration of a vic-tricarbonyl compound (see scheme; TES=triethylsilyl). A stereoselective alkene dihydroxylation followed by a differentiation of diastereotopic ester groups and a subsequent lactamization gave the bicyclic core structure. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by 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

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