The synthesis of 2,6-dihydroxy-7,8-dimethoxy-9,10-dihydro-5H-phenanthro[4,5-bcd]pyran-5-one (coeloginin)(1), a natural product isolated from the orchid Coelogyne cristata, is described. The key step involved the treatment of methyl 9,10-dihydro-5,7-di-isppropoxy-1,2,3-trimethoxyphenanthrene-4-carboxylate (12) with boron trichloride which gave coeloginin (1) directly.
M. V. Sargent and E. Stanojevic, J. Chem. Soc., Perkin Trans. 1, 1984, 1919 DOI: 10.1039/P19840001919
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