Synlett 2015; 26(15): 2151-2155
DOI: 10.1055/s-0034-1378831
letter
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Angularly Fused Pyranochromenes

Barnali Sarmah
a   Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat-785006, Assam, India   Email: b.gakul@gmail.com
,
Gakul Baishya*
a   Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat-785006, Assam, India   Email: b.gakul@gmail.com
,
Nabajyoti Hazarika
a   Natural Products Chemistry Division, CSIR-North East Institute of Science & Technology, Jorhat-785006, Assam, India   Email: b.gakul@gmail.com
,
Pranab Jyoti Das
b   Department of Chemistry, Gauhati University, Guwahati-781014, Assam, India
› Author Affiliations
Further Information

Publication History

Received: 07 May 2015

Accepted after revision: 02 July 2015

Publication Date:
14 August 2015 (online)


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.

Supporting Information

 
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  • 19 Pyrano[3,2-c]chromenes 3ak; 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.