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Org Lett. 2014 Apr 4;16(7):1956-9. doi: 10.1021/ol5005092. Epub 2014 Mar 27.

Stereocontrolled synthesis of the tricyclic ABC ring system of daphnicyclidin A.

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  • 1Department of Chemistry, Indiana University , Bloomington, Indiana 47405, United States.


An enantiocontrolled synthesis pathway has been developed to provide formation of tricyclic amine 7, representing the ABC ring system of the complex alkaloid daphnicyclidin A (1). Our efforts describe preparation of the Z-hexahydro-(1H)-azocine 29 and cyclization to construct the novel 4-azabicyclo[5.3.2]dodecane 31. Transannular reductive amination following the deprotection of 31 gave the desired tertiary amine 7.

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