Template-directed C H activation: development and application to the total synthesis of 7-episordidin

DJ Wardrop, RE Forslund, CL Landrie, AI Velter…

Index: Wardrop, Duncan J.; Forslund, Raymond E.; Landrie, Chad L.; Velter, Adriana I.; Wink, Donald; Surve, Bushan Tetrahedron Asymmetry, 2003 , vol. 14, # 7 p. 929 - 940

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Citation Number: 21

Abstract

The development of a template-directed C H activation strategy and its application to the diastereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of the synthetic route is a regioselective rhodium (II)-catalyzed diazocarbonyl C H activation reaction that simultaneously generates three of the four stereocenters present in the natural product.