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Synthetic studies on azadirachtin (Part 3): Asymmetric synthesis of the tricyclic dihydrofuran moiety of azadirachtin

✍ Scribed by Jun Ishihara; Takehiro Fukuzaki; Akio Murai

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
224 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

An asymmetric synthesis of the tricyclic dihyctrofuran moiety of azadirachtin is reported. The Diels-Alder adduct, which was catalyzed by Evans' chiral Cu-bisoxazoline complex, was easily converted to the tricyclic portion via SmI 2 reductive cleavage and selective functionalization.

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Construction of the left segment of azadirachtin in naturally occurring enantiomer is described. The key reaction is an intramolecular Diels-Alder reaction, which was performed under thermal conditions to afford the highly functionalized decalin compounds selectively.