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- Title
Asymmetric Formal Synthesis of Azadirachtin.
- Authors
Mori, Naoki; Kitahara, Takeshi; Mori, Kenji; Watanabe, Hidenori
- Abstract
An asymmetric formal synthesis of azadirachtin, a potent insect antifeedant, was accomplished in 30 steps to Ley's synthetic intermediate (longest linear sequence). The synthesis features: 1) rapid access to the optically active right-hand segment starting from the known 5-hydroxymethyl-2-cyclopentenone scaffold; 2) construction of the B and E rings by a key intramolecular tandem radical cyclization; 3) formation of the hemiacetal moiety in the C ring through the a-oxidation of the six-membered lactone followed by methanolysis.
- Subjects
ASYMMETRY (Chemistry); AZADIRACHTIN; CYCLOPENTENONE; FUNCTIONAL groups; RING formation (Chemistry); LACTONES; METHANOLYSIS; HYDROXYMETHYL compounds
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 49, p15133
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201507935