Enantioselective Synthesis of (–)-Maoecrystal V by Enantiodetermining C—H Functionalization

Ping Lu , Artur Mailyan , Zhenhua Gu , David Guptill , Hengbin Wang , Huw M. L. Davies , and Armen Zakarian

J. Am. Chem. Soc.,
2014, 136, (51), 17738-17749; 10.1021/ja510573v


A collaborative project between the Zakarian and Davies group marks the first asymmetric synthesis of the natural enantiomer of maoecrystal V, confirming the assigned stereochemistry.

Maoecrystal V, a highly modified ent-kauranoid is the subject of many current synthetic endeavors, both because of its unusual and challenging structural architecture, but also its potent cytotoxic activity.

This approach employs an early stage intramolecular chiral auxiliary-directed asymmetric C–H functionalization for the construction of a key benzofuran intermediate that sets the stereochemistry for the synthetic strategy.

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