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Enantioselective Total Synthesis of Four Styrylpyrone Derivatives

Enantioselective Total Synthesis of Four Styrylpyrone Derivatives
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摘要 The first enantioselective total synthesis of 5-acetoxygoniothalamin 1 and 5-acetoxyisogoniothalamin oxide 2 was achieved through the Sharpless kinetic resolution of racemic secondary 2- furylmethanol 5 and the Mitsunobu reaction. At the same time we developed a short synthetic route for 6R-(+)-goniothalamin 3 and (6R, 7R, 8R)-(+)-goniothalamin oxide 4. And according to this route the configuration of 5-acetoxygoniothalamin 1 was confirmed as (5S, 6S). The first enantioselective total synthesis of 5-acetoxygoniothalamin 1 and 5-acetoxyisogoniothalamin oxide 2 was achieved through the Sharpless kinetic resolution of racemic secondary 2- furylmethanol 5 and the Mitsunobu reaction. At the same time we developed a short synthetic route for 6R-(+)-goniothalamin 3 and (6R, 7R, 8R)-(+)-goniothalamin oxide 4. And according to this route the configuration of 5-acetoxygoniothalamin 1 was confirmed as (5S, 6S).
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2002年第6期519-520,共2页 中国化学快报(英文版)
基金 We are grateful to the National Natural Science Foundation of China(No.2017223)for financial support
关键词 ENANTIOSELECTIVE 5-acetoxygoniothalamin 5-acetoxyisogoniothalamin oxide 6R-(+)- goniothalamin (6R 7R 8R)-(+)-goniothalamin oxide. Enantioselective 5-acetoxygoniothalamin 5-acetoxyisogoniothalamin oxide 6R-(+)- goniothalamin (6R, 7R, 8R)-(+)-goniothalamin oxide.
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参考文献8

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  • 8[8]Compound 8: [α]25 D +93 (c 0.4, CHCl3), IR (KBr, cm-1): 1680, 1640; m/z (EI) 229 (M+-45), 131, 115, 103; 1HNMR (400MHz, CDCl3) 1.21 and 1.24 (each t, 3H, J=7.2Hz), 1.41 and 1.43 (each d, 3H, J=4.8 Hz), 2.12-2.25 (m, 2H), 3.53-3.74 (m, 2H), 4.58 (m, 1H), 4.96 and 5.03 (each q, 1H, J=5.6 Hz, OCHMe ), 5.27 and 5.37 (each br s , 1H), 5.75 and 5.81 (m, 1H), 6.09 (m, 1H), 6.27 (dd, 1H, J=16.2 and 5.9 Hz), 6.65 (d, 1H, J =16.2 Hz) and 7.25-7.43 (m, 5H).

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