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CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .8. SYNTHESIS OF HYDROXYDIHYDROFURAN ACETAL FRAGMENTS FOR BIOLOGICAL EVALUATION AND AZADIRACHTIN TOTAL SYNTHESIS STUDIES

ANDERSON, JC; LEY, SV; SANTAFIANOS, D; SHEPPARD, RN; (1991) CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .8. SYNTHESIS OF HYDROXYDIHYDROFURAN ACETAL FRAGMENTS FOR BIOLOGICAL EVALUATION AND AZADIRACHTIN TOTAL SYNTHESIS STUDIES. TETRAHEDRON , 47 (33) 6813 - 6850.

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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.

Type:Article
Title:CHEMISTRY OF INSECT ANTIFEEDANTS FROM AZADIRACHTA-INDICA .8. SYNTHESIS OF HYDROXYDIHYDROFURAN ACETAL FRAGMENTS FOR BIOLOGICAL EVALUATION AND AZADIRACHTIN TOTAL SYNTHESIS STUDIES
Keywords:METAL PEROXIDE REACTIONS, TERPENOID ANTIFEEDANTS, NMR, HYDROXYLATION, INTERMEDIATE, ALCOHOLS, DECALIN, ETHERS, FK-506
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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