Diastereoselective Synthesis of Angularly Fused Pyranochromenes

Abstract

o-Quinonemethides generated by condensation of 6-methylhept-5-en-2-ol with various salicylaldehydes in the presence of 30 mol% of fluoroboric acid etherate or triflic acid undergo [4+2]-cycloaddition reaction in situ to afford angularly fused pyranochromene derivatives in good yields and excellent diastereoselectivities.

Key words

aldehydes - condensations - cycloadditions - heterocycles - fused-ring systems

• References

• 1 Classics in Total Synthesis: Targets, Strategies, Methods . Nicolaou KC, Sorensen EJ. Wiley-VCH; Weinheim: 1996
• 2a Arundale E, Mikeska LA. Chem. Rev. 1952; 51: 505
• 2b Adams DR, Bhatnagar SP. Synthesis 1977; 661
• 2c Snider BB In: Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Chap. 2.1 Pergamon; Oxford: 1991: 527
• 2d Bratz M, Bullock WH, Overman LE, Takemoto TJ. J. Am. Chem. Soc. 1995; 117: 5958
• 2e Charonat JA, Nishimura NB, Travers W, Waas JR. Synlett 1996; 1162
• 2f Pansare SV, Jain RP. Org. Lett. 2000; 2: 175
• 2g Marumoto S, Jaber JJ, Vitale JP, Rychnovsky SD. Org. Lett. 2002; 4: 3919
• 2h Cossey KN, Funk RL. J. Am. Chem. Soc. 2004; 126: 12216
• 2i Dalgard JE, Rychnovsky SD. Org. Lett. 2005; 7: 1589
• 2j Vitale JP, Wolckenhauer SA, Do NA, Rychnovsky SD. Org. Lett. 2005; 7: 3255
• 2k Meilert K, Brimble MA. Org. Lett. 2005; 7: 3497
• 2l Miranda LS. M, Meireles BA, Costa JS, Pereira VL. P. Synlett 2005; 869
• 2m Barry CS, Busby N, Harding JR, Willis CL. Org. Lett. 2005; 7: 2683
• 2n Aubele DL, Wan S, Floreancig PE. Angew. Chem. 2005; 117: 3551 ; Angew. Chem. Int. Ed. 2005, 44, 3485
• 2o Yang X.-F, Wang M, Zhang Y, Li C.-J. Synlett 2005; 1912
• 2p Tian X, Jaber JJ, Rychnovsky SD. J. Org. Chem. 2006; 71: 3176
• 2q Chan K.-P, Ling YH, Loh T.-P. Chem. Commun. 2007; 939
• 2r Ko HY, Lee DG, Kim MA, Kim HJ, Park JM, Lah S, Lee E. Org. Lett. 2007; 9: 141
• 2s Yadav JS, Kumar NN, Reddy MS, Prasad AR. Tetrahedron 2007; 63: 2689
• 2t Yadav JS, Rao PP, Reddy MS, Rao NV, Prasad AR. Tetrahedron Lett. 2007; 48: 1469
• 3a Evans DA, Wu J. J. Am. Chem. Soc. 2005; 127: 8006
• 3b Overman LE. Acc. Chem. Res. 1992; 25: 352
• 3c Loh T.-P, Feng L.-C, Yang J.-Y. Synthesis 2002; 937
• 3d Blumenkopf TA, Look GC, Overman LE. J. Am. Chem. Soc. 1990; 112: 4399
• 3e Overman LE, Thompson AS. J. Am. Chem. Soc. 1988; 110: 2248
• 3f Loh T.-P, Yang J.-Y, Feng L.-C, Zhou Y. Tetrahedron Lett. 2002; 43: 7193
• 4a Chen S.-L, Hu Q.-Y, Loh T.-P. Org. Lett. 2004; 6: 3365
• 4b Sonawane HR, Jana GH. Chem. Commun. 1998; 1773
• 4c Saha P, Ghosh P, Sultana S, Saikia AK. Org. Biomol. Chem. 2012; 10: 8730
• 4d Bondalapati S, Reddy UC, Saha P, Saikia AK. Org. Biomol. Chem. 2011; 9: 3428
• 4e Saha P, Reddy UC, Bondalapati S, Saikia AK. Org. Lett. 2010; 12: 1824
• 4f Saha P, Saikia AK. Tetrahedron 2012; 68: 2261
• 5a Miyazaki H, Honda K, Asami M. Inoue S. 1999; 64: 9507
• 5b Inoue S, Asami M, Honda K, Miyazaki H. Chem. Lett. 1996; 10: 889
• 6 Banskota H, Tezuka Y, Prasain JK, Matsushige K, Saiki I, Kadota S. J. Nat. Prod. 1998; 61: 896
• 7 McKee TC, Fuller RW, Covington CD, Cardellina JH, Gulakowski RJ, Krepps BL, McMahon JB, Boyd MR. J. Nat. Prod. 1996; 59: 754
• 8a Ashwood VA, Cassidy F, Coldwell MC, Evans JM, Hamilton TC, Howlett DR, Smith DM, Stemp G. J. Med. Chem. 1990; 33: 2667
• 8b Cassidy F, Evans JM, Hadley MS, Haladij AH, Leach PE, Stemp G. J. Med. Chem. 1992; 35: 1623
• 9a Atwal KS, Grover GJ, Ferrara FN, Ahmed SZ, Sleph PG, Dzwonczyk S, Normandin DE. J. Med. Chem. 1995; 38: 1966
• 9b Atwal KS, Grover GJ, Ahmed SZ, Ferrara FN, Harper TW, Kim KS, Sleph PG, Dzwonczyk S, Russell AD, Moreland S, McCullough JR, Normandin DE. J. Med. Chem. 1993; 36: 3971
• 10a Martin BR, Lichtman AH. Neurobiol Dis. 1998; 5: 447
• 10b Pertwee RG. Euphytica 2004; 140: 73
• 10c Mechoulam R. Br. J. Pharmacol. 2005; 146: 913
• 11a Marsicano G, Goodenough S, Monory K, Hermann H, Eder M, Cannich A, Azad SC, Cascio MG, Gutiérrez SO, van der Stelt M, López-Rodriguez ML, Casanova E, Schütz G, Zieglgänsberger W, Di Marzo V, Behl C, Lutz B. Science 2003; 302: 84
• 11b Eubanks LM, Rogers CJ, Beuscher T, Janda KD. Mol. Pharmaceutics. 2006; 3: 773
• 12 Loh T.-P, Hu Q.-Y, Tan K.-T, Cheng H.-S. Org. Lett. 2001; 3: 2669
• 13 Raju NP, Reddy BJ. M, Anjibabu R, Muralikrishna K, Subba Reddy BV. Tetrahedron Lett. 2013; 54: 3639
• 14a Uddin N, Ulicki JS, Foersterling FH, Hossain MM. Tetrahedron Lett. 2011; 52: 4353
• 14b Molander GA, Raushel J, Ellis NM. J. Org. Chem. 2010; 75: 4304
• 14c Akiyama T, Itoh J, Fuchibe K. Synlett 2002; 1269
• 14d Islam MS, Brenan C, Wang Q, Hossain MM. J. Org. Chem. 2006; 71: 4675
• 14e Dudely ME, Morshed MM, Brenan CL, Islam MS, Ahmad MS, Attu M.-R, Branstetter B, Hossain MM. J. Org. Chem. 2004; 69: 7599
• 14f Subba Reddy BV, Reddy NS, Madan Ch, Yadav JS. Tetrahedron Lett. 2010; 51: 4827
• 15a Yadav JS, Subba Reddy BV, Anusha B, Subba Reddy UV, Bhadra Reddy VV. Tetrahedron Lett. 2010; 51: 2872
• 15b Yadav JS, Subba Reddy BV, Ramesh K, Narayana Kumar GG. K. S, Grée R. Tetrahedron Lett. 2010; 51: 1578
• 16a Sarmah B, Baishya G, Baruah RK. Eur. J. Org. Chem. 2014; 7561
• 16b Hazarika N, Baishya G. Eur. J. Org. Chem. 2014; 5686
• 16c Baishya G, Hazarika N, Sarmah B. J. Fluorine Chem. 2014; 166: 1
• 16d Hazarika N., Baishya G., Phukan P.; Synthesis; 2015, 47: in press; DOI: 10.1055/s-0034-1380754.
• 17a Olah GA, Wu A. J. Org. Chem. 1991; 56: 2531
• 17b Rosenfeld DC, Shekhar S, Takemiya A, Utsunomiya M, Hartwig JF. Org. Lett. 2006; 8: 4179
• 17c Praveen C, Parthasarathy K, Perumal PT. Synlett 2010; 1635
• 17d Kumbhare RM, Sridhar M. J. Chem. Sci. (Amritsar, India) 2012; 124: 495
• 17e Sarmah B, Baishya G, Baruah RK. RSC Adv. 2014; 4: 22387
• 18 Baishya G, Sarmah B, Hazarika N. Synlett 2013; 24: 1137
• 19 Pyrano[3,2-c]chromenes 3a–k; General Procedure HBF₄·OEt₂ (Method A) or TfOH (Method B) (0.3 mmol, 0.3 equiv) was added slowly to a solution of 6-methylhept-5-en-2-ol (1; 2.0 mmol, 2.0 equiv) and salicylaldehyde 2 (1.0 mmol, 1.0 equiv) in anhyd CH₂Cl₂ (2 mL) at 0 °C, and the mixture was stirred at 0 °C for 3–5 h. When the reaction was complete (TLC), sat. aq NaHCO₃ (10 mL) was added, and the mixture was extracted with EtOAc (3 ×10 mL). The organic layer was washed with brine (10 mL), dried (Na₂SO₄), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel (100–200 mesh), EtOAc–hexane (1:99)]. Spectroscopic data for all synthesized compounds are presented in the Supporting Information. (2R*,4aR*,10bR*)-7-Bromo-2,5,5-trimethyl-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c]chromene (3f) Brownish solid; yield: 221 mg (71%, Method A); mp 72 °C; IR (CHCl₃): 2925.0, 1448.2, 1370.1, 1320.3, 1256.8, 1138.8, 932.2 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 7.41–7.37 (m, 2 H), 6.77–6.73 (m, 1 H), 4.24 (d, J = 11.0 Hz, 1 H), 3.70–3.68 (m, 1 H), 1.90 (m, 1 H), 1.78 (m, 1 H), 1.65–1.61 (m, 1 H), 1.45 (s, 3 H), 1.41–1.29 (m, 2 H), 1.28 (d, J = 4.0 Hz, 3 H), 1.25 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 149.48, 136.85, 132.14, 125.31, 120.46, 110.51, 79.71, 73.74, 72.68, 44.29, 33.20, 27.48, 25.08, 21.75, 20.45. MS (EI): m/z = 312 [M + H]⁺, 313 [M + 2]⁺. Anal. Calcd for C₁₅H₁₉BrO₂: C, 57.89; H, 6.15. Found: C, 57.95; H, 6.20. (2R*,4aR*,10bR*)-2,5,5-Trimethyl-9-nitro-3,4,4a,10b-tetrahydro-2H,5H-pyrano[3,2-c]chromene (3h) Yellowish solid; yield: 194 mg (70%, Method A); mp 127 °C. IR (CHCl₃): 2976.8, 2934.2, 2852.5, 1619.7, 1587.5, 1516.6, 1479.1, 1338.4, 1272.0, 1134.8, 1095.8, 966.0, 750.4 cm^–1. ¹H NMR (500 MHz, CDCl₃): δ = 8.39 (s, 1 H), 8.02 (dd, J = 10.5, 2.5 Hz, 1 H), 6.82 (d, J = 9.0 Hz, 1 H), 4.23 (d, J = 10.0 Hz, 1 H), 3.76–3.70 (m, 1 H), 1.94–1.90 (m, 1 H), 1.89–1.80 (m, 1 H), 1.63 (m, 1 H), 1.42 (s, 3 H), 1.40–1.33 (m, 2 H), 1.28 (d, J = 6.5 Hz, 3 H), 1.25 (s, 3 H). ¹³C NMR (125 MHz, CDCl₃): δ = 158.39, 140.78, 124.54, 122.94, 122.89, 117.15, 80.74, 73.97, 71.76, 43.99, 33.03, 27.34, 24.88, 21.63, 20.73. MS (EI): m/z = 277 [M]⁺, 278 [M + H]⁺. Anal. Calcd for C₁₅H₁₉NO₄: C, 64.97; H, 6.91; N, 5.05. Found: C, 65.03; H, 6.95; N, 5.11.