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Fig. 3 Reaction mechanism showing energy calculations at each step.
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Fig. 4 Synthesis of ER-b agonist 2vh. Reagents and conditions: (a) n-BuLi,
THF, 30 min, 0 1C, 92%; (b) 50% TFA in water, 80 1C, 0.5 h, 92%; (c) BBr3,
anhydrous DCM, rt, 3 h, 84%.
transition state for the concerted Diels–Alder reaction with a
barrier of about 40.58 kcal molꢀ1
.
Further, the newly established protocol was utilized for
synthesis of 7,40-dihydroxy-2-phenylnaphthalene 2vh which
has been reported as a potent and selective agonist of estrogen
receptor-b (IC50 44 nM).1d The synthetic scheme for the preparation
of ER-b agonist 2vh is depicted in Fig. 4.
In conclusion, we have developed a new method for the synthesis
of 2-phenylnaphthalenes from 1-styryl-methoxybenzenes. Using
quantum chemical calculations, the mechanism of the reaction
has been established. The utility of the established protocol for
synthesis of the phenanthrene scaffold and the potent naphthalene-
based selective ER-b agonist has been demonstrated.
The authors thank analytical department IIIM for analytical
support. RM, RS and SA are thankful to CSIR, DST and UGC for
research fellowships. Financial support from DST-SERB is
gratefully acknowledged (grant no. SR/FT/CS-168/2011).
Notes and references
1 For applications of naphthalene scaffold, see: (a) S. V. Bhosale,
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9535–9546; (c) S. Akutagawa, Appl. Catal., A, 1995, 128, 171–207;
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B. W. A. Vanhoecke, A. R. Katritzky, M. E. Bracke and C. V. Stevens,
Bioorg. Med. Chem., 2013, 21, 5054–5063.
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Chem. Commun., 2014, 50, 12076--12079 | 12079