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(6bR*,9aR*)-6-(2-Benzyloxy-1-oxoethyl)-6b,9a-dihydro-5-hydroxy- 4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

Margaret A. Brimble
* and
Josephine S. O. Park
School of Chemistry, University of Sydney, Eastern Ave, Camperdown, NSW 2006, Australia
Author to whom correspondence should be addressed.
Molecules 2000, 5(2), M134;
Submission received: 20 January 2000 / Accepted: 2 February 2000 / Published: 23 February 2000
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 05 m134 i001
A solution of ceric ammonium nitrate (37 mg, 0.067 mmol) in water was added dropwise to a vigorously stirred solution of naphthol 1 (13 mg, 0.036 mmol) [1] in acetonitrile (2.2 mL) at room temperature and stirred for 15 min. Anhydrous magnesium sulfate was added and the resultant suspension immediately cooled to 0°C. After 1min., a solution of 2-trimethylsilyloxyfuran 2 (0.012 mL, 0.071 mmol) in acetonitrile (0.2 mL) was added dropwise and the resultant solution stirred at 0°C for 30 min. The reaction mixture was diluted with dichloromethane (5 mL), washed with water (2 × 3 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure to give an orange oil, which was then purified by flash chromatography using light petroleum-ethyl acetate (4:1) as eluent to afford the title compound 3 (9 mg, 60%) as a yellow oil.
IR (cm−1, neat): 3320w, 1785s, 1731, 1077.
1H NMR (200 MHz, CDCl3): 3.10–3.12 (2H, m, H9), 4.12 (3H, s, OMe), 4.67 (1H, d, Jgem 12.0 Hz, OCHAPh), 4.77 (1H, d, Jgem 18.1 Hz, COCHA), 4.88 (1H, d, Jgem 12.0 Hz, OCHBPh), 4.95 (1H, d, Jgem 18.1 Hz, COCHB), 5.43–5.49 (1H, m, H9a), 6.80 (1H, d, J6b,9a 6.1 Hz, H6b), 6.98 (1H, J3,2 7.0 and J3,1 2.0 Hz, H3), 7.28–7.60 (7H, m, H1, H2, Ph), 10.46 (1H, s, OH).
EI-MS: 420 (M+, 2%), 299 (M-CH2OBn, 25), 269 (M-C9H11O2, 13), 149 (COCH2OBn, 15), 91 (C7H7, 100), 57 (CH3CH2CO, 67), 43 (CH3CO, 54).
Anal. calc. for C24H20O7 MH+ (CI, NH3), 421.1286; found MH+, 421.1287.

Supplementary Materials


  1. Brimble, M.A.; Oppen, E. Synth. Commun. 1997, 27, 989–1007. [CrossRef]
Sample Availability: Available from the authors.

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MDPI and ACS Style

Brimble, M.A.; Park, J.S.O. (6bR*,9aR*)-6-(2-Benzyloxy-1-oxoethyl)-6b,9a-dihydro-5-hydroxy- 4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one. Molecules 2000, 5, M134.

AMA Style

Brimble MA, Park JSO. (6bR*,9aR*)-6-(2-Benzyloxy-1-oxoethyl)-6b,9a-dihydro-5-hydroxy- 4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one. Molecules. 2000; 5(2):M134.

Chicago/Turabian Style

Brimble, Margaret A., and Josephine S. O. Park. 2000. "(6bR*,9aR*)-6-(2-Benzyloxy-1-oxoethyl)-6b,9a-dihydro-5-hydroxy- 4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one" Molecules 5, no. 2: M134.

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