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J Am Chem Soc. 2012 Dec 26;134(51):20605-8. doi: 10.1021/ja310482z. Epub 2012 Dec 10.

Ivorenolide A, an unprecedented immunosuppressive macrolide from Khaya ivorensis: structural elucidation and bioinspired total synthesis.

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  • 1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China.


Ivorenolide A (1), a novel 18-membered macrolide featuring conjugated acetylenic bonds and five chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis, single-crystal X-ray diffraction, and bioinspired total synthesis. Both compound 1 and its synthetic enantiomer 2 showed potent and selective immunosuppressive activity.

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