Synthetic studies on azadirachtin: stereoselective construction of the ABCE ring system |
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| Authors: | Daisuke Nakagawa Keiji Tanino |
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| Affiliation: | a Division of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
b Department of Applied Chemistry, Faculty of Engineering, Kogakuin University, Hachioji 192-0015, Japan |
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| Abstract: | A new method for constructing the ABCE ring system of azadirachtin in a stereoselective manner was developed. The synthesis of the model compound features (1) stereoselective construction of the highly hindered C8 quaternary center by an intermolecular addition reaction of an allylborane with an aldehyde and (2) construction of the E ring moiety by the Pd-catalyzed Nazarov cyclization. |
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