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Synthetic studies on azadirachtin: stereoselective construction of the ABCE ring system

✍ Scribed by Daisuke Nakagawa; Masaaki Miyashita; Keiji Tanino

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
517 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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