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Synthesis of the tricyclic dihydrofuran moiety of azadirachtin: efficient transformation of the Claisen rearrangement intermediate into a functionalized tricyclic dihydrofuran core

โœ Scribed by Jun Ishihara; Yohei Ikuma; Susumi Hatakeyama; Takanori Suzuki; Akio Murai


Book ID
108282425
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
254 KB
Volume
59
Category
Article
ISSN
0040-4020

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Synthetic studies on azadirachtin (Part
โœ Jun Ishihara; Takehiro Fukuzaki; Akio Murai ๐Ÿ“‚ Article ๐Ÿ“… 1999 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 224 KB

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.