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Dalbergichromene:A new neoflavonoid from stem-bark and heartwood of Dalbergia sissoo

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
27
Issue
4
Identifiers
DOI: 10.1016/s0040-4020(01)92474-3

Abstract

Abstract The stem-bark of Dalbergia sissoo has yielded, besides the known compounds dalbergenone, dalbergin and methyl dalbergin, a new 4-phenyl chromene, dalbergichromene. Its structure has been determined as 7-methoxy-6-hydroxy-4-phenyl chrom-3-ene by spectral and degradative experiments and confirmed by rearrangement of dalbergenone to dalbergichromene. Reinvestigation of the heartwood shows that in addition to the known compounds the plant also contains dalbergichromene, nordalbergin and isodalbergin as minor constituents. A new method of conversion of 4-phenylcoumarins into 4-phenylchromenes involves cyclodehydration of the appropriate ortho hydroxy cinnamyl alcohols.

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