Citation: Jin-Hui Yang, Bing-Bing Chen, Yi-Min Xie, Yao Feng, Xiao-Qin Ma. First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B[J]. Chinese Chemical Letters, ;2013, 24(11): 1027-1029. shu

First total synthesis of (±)-malaysianone A and (±)-tanariflavanones B

1.
State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021, China

Corresponding author: Jin-Hui Yang,
Received Date: 16 May 2013
Available Online: 21 June 2013

A concise approach for the first total synthesis of two naturally occurring flavanoids, (±)-malaysianone A (1) and (±)-tanariflavanones B (2), has been accomplished with total yields of 12.9% and 10.4%, respectively. The key steps were regioselective deprotection and regioselective synthesis of 5-formaldehyde-8-hydroxy-2-[40-methyl-30-penteneyl]-dihydro-1-benzopyran (8).
- Malaysianone A,
- Tanariflavanones B,
- Total synthesis,
- Flavanoids
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  [16] Spectral data of (±)-malaysianone A: White solid, mp 89-91 ℃; ¹H NMR (400 MHz, CDC_l3): δ 12.06 (s, 1H, OH-5), 6.91 (dd, 1H, J = 1.6 Hz, J = 8.4 Hz, H-50), 6.85 (d, 1H, J = 8.0 Hz, H-60), 6.61 (d, 1H, J = 10 Hz, H-200), 6.18 (s, 1H, OH-40), 6.01 (d, 1H, J = 2.4 Hz, H-6), 5.98 (d, 1H, J = 2.4 Hz, H-8), 5.69 (d, 1H, J = 10.4 Hz, H-100), 5.60 (s, 1H, OH-7), 5.53 (dd, 1H, J = 2.8 Hz, J = 13.2 Hz, H-2), 5.08 (dt, 1H, J = 1.2 Hz, J = 5.6 Hz, H-700), 3.15 (dd, 1H, J = 13.2 Hz, J = 17.2 Hz, H-3_ax), 2.75 (dd, 1H, J = 3.2 Hz, J = 17.2 Hz, H-3_eq), 2.10-2.06 (m, 2H, H-600), 1.79-1.68 (m, 2H, H-500), 1.67, 1.57 (s, 6H, 2×CH₃, H-900 and 1000), 1.43 (d, 3H, J = 6.0 Hz, CH₃, H-400); ¹³C-NMR (100 MHz, CDC_l3,): δ 196.4 (s, C-4), 164.9 (s, C-7), 164.2 (s, C-5), 163.3 (s, C-9), 145.0 (s, C-40), 139.6 (s, C-30), 132.1 (s, C-800), 131.0 (s, C-200), 124.6 (s, C-10), 123.6 (s, C-700), 118.9 (s, C-20), 118.8(d, C-60), 118.6 (s, C-100), 114.5 (s, C-50), 103.0 (s, C-10), 96.8 (s, C-8), 95.6 (s, C-6), 79.0 (s, C-300), 76.0 (d, C-2), 42.3 (s, C-3), 40.7 (s, C-500), 26.0 (d, C-400), 25.6 (s, C-1000), 22.7 (s, C-600), 17.6 (s, C-900). HREIMS (m/z): 423.18039 [M+H]⁺ (calcd. for C₂₅H₂₆O₆: 423.18022). Spectral data of (±)-tanariflavanones B (C₃₀H₃₄O₆): Brownish oil, ¹HNMR (400 MHz, CDC_l3,): d 12.4 (s, 1H, OH-5), 6.90 (d, 1H, J = 8.4 Hz, H-60), 6.84 (d, 1H, J = 8.4 Hz, H-50), 6.60 (d, 1H, J = 10 Hz, H-100), 6.33 (s, 1H, OH-40), 5.99 (s, 1H, H-8), 5.68 (d, 1H, J = 10 Hz, H-200), 5.60 (s, 1H, OH-7), 5.50 (dd, 1H, J = 13.6 Hz, J = 2.8 Hz, H-2), 5.24 (dt, 1H, H-2000), 5.08 (dt, 1H, H-700), 3.35 (d, 2H, J = 7.2 Hz, H-1000), 3.16 (dd, 1H, J = 13.2 Hz, J = 17.2 Hz, H-3_ax), 2.75 (dd, 1H, J = 2.8 Hz, J = 17.2 Hz, H-3_eq), 2.10-2.12 (m, 2H, CH2, H-600), 1.82-1.77 (m, 2H, H-500), 1.57, 1.67, 1.72, 1.75 (s, 12H, 4CH₃), 1.42 (d, 3H, CH₃); ¹³CNMR(100 MHz, CDC_l3,): d 196.3 (s, C-4), 163.7 (s, C-7), 161.3 (s, C-9), 161.1 (s, C-5), 145.1 (s, C-40), 139.6 (s, C-30), 135.5 (s, C-3000), 132.1 (s, C-800), 130.9 (d, C-200), 124.8 (d, C-700), 123.6 (s, C-10), 121.5 (d, C-2000), 118.9 (d, C-100), 118.7 (d, C-60), 118.6 (s, C-20), 114.5 (d, C-50), 107.1 (s, C-6), 102.9 (s, C-10), 95.5 (d, C-8), 79.0 (s, C-300), 76.0 (d, C-2), 42.5 (d, C-3), 40.7 (s, C-500), 26.1 (d, C-400), 25.8 (s, C-4000), 25.6 (s, C-1000), 22.7 (s, C-600), 21.1 (s, C-1000), 17.8 (d, C-5000), 17.6 (s, C-900). HREIMS (m/z): 491.2440 [M+H]⁺.
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沈阳化工大学材料科学与工程学院沈阳 110142