K. Samanta et al. / Tetrahedron Letters 53 (2012) 1376–1379
1379
Table 3
Thus in conclusion, the work describes a short and generalised
approach for the synthesis of hydroxyphenanthrenes and related
polycyclic aromatic hydroxy compounds starting from easily
Synthesis of polycyclic aromatic hydroxyl compounds (9)
Entry Reactant (crude) Product
Isolated yield (%)
available b-furyl-a,b-unsaturated aldehydes. Synthesis of some
OH
natural products may be achieved by this strategy using suitably
substituted furan moiety and the work will be taken up in due
time.
1
2
3
7a
7b
7c
48
9a8
Acknowledgments
OH
Financial help from CSIR and DST acknowledged gratefully. We
are thankful to CSIR for providing NET fellowship to one of the
authors (K.S.). We are also thankful to Professor J.K. Ray, Depart-
ment of Chemistry, I.I.T Kharagpur-721302, India, for providing
us with few 1H NMR spectral data of our synthesised compounds.
42
40
HO
9b9
OH
Supplementary data
Supplementary data associated with this article can be found, in
MeO
9c9
OH
OMe
References and notes
MeO
MeO
4
5
7d
7e
35
—
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Haworth, R. D. J. Chem. Soc. 1932, 12, 1125.
9d
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No characterisable product
6
7
7f
52
—
9f10
OH
7g
No characterisable product
OH
6. (a) Hashmi, A. S. K.; Frost, T. M.; Bats, J. W. J. Am. Chem. Soc. 2000, 122, 11553;
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8
9
7h
7i
35
—
9h11
No characterisable product
´
8. Barbasiewicz, M.; Szadkowska, A.; Makal, A.; Jarzembska, K.; Wozniak, K.;
Grela, K. Chem. Eur. J. 2008, 14, 9330.
Diels–Alder reaction. The product mixture contained large number
of spots in TLC and we were unable to isolate the components in
pure form for characterisation.
9. Cornforth, J. W.; Robinson, R. J. Chem. Soc. 1942, 684.
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