Synthesis and X-Ray Crystal Structure of Cynandione B Analogues
Lisa P. T. Hong A B , Jonathan M. White A B and Christopher D. Donner A B CA School of Chemistry, The University of Melbourne, Vic. 3010, Australia.
B Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Vic. 3010, Australia.
C Corresponding author. Email: cdonner@unimelb.edu.au
Australian Journal of Chemistry 65(1) 58-64 https://doi.org/10.1071/CH11364
Submitted: 12 September 2011 Accepted: 10 November 2011 Published: 12 December 2011
Abstract
The synthesis of analogues of cynandione B, a phenolic acetophenone from Cynanchum taiwanianum, is described. The one-step conversion of benzochromenones to the heptacyclic spiroacetal core of cynandione B using methylmagnesium bromide is investigated and structural requirements for this novel transformation established. X-ray crystal structure analysis has established the relative configuration in these unusual heterocycles.
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