Abstract
The work describes a unified strategy towards the preparation of model hydroxydihydrofuran acetal fragments (2) (3) and (45) common to the potent insect antifeedant and growth disruption agent azadirachtin (1). These units, along with other analogues, were prepared for biological evaluation as antifeedants. Furthermore, several potential coupling fragments (51), (52), (54), (55), (62), (63) and (56) for azadirachtin synthesis were also prepared from common precursors. Methods were developed to prepare these materials in enantiomerically pure form and to conveniently protect the angular hydroxyl group and unmask the labile enol double bond at a late stage in the synthesis.
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