Combined directed ortho metalation/cross-coupling strategies: synthesis of the tetracyclic A/B/C/D ring core of the antitumor agent camptothecin |
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| Authors: | Nguyen Tam Wicki Markus A Snieckus Victor |
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| Institution: | The Guelph-Waterloo Centre for Graduate Work in Chemistry, Department of Chemistry, University of Waterloo, Waterloo, ON, Canada N2L 3G1. |
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| Abstract: | A convergent synthesis of the A/B/C/D ring fragment 5 of camptothecin using a combination of directed ortho metalation and Negishi cross-coupling is described. The key features of the synthetic sequence are an anionic ortho-Fries rearrangement (10 --> 12), a Negishi cross-coupling (7 --> 6), and a terminal modified von Braun reaction (16 --> 5) that leads to tetracyclic derivative 5 in 7 steps and 11% overall yield. |
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