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Rapid construction of the tricyclic cores of the abietane- and icetexane-type diterpenoids

Rapid construction of the tricyclic cores of the abietane- and icetexane-type diterpenoids
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摘要 A short synthesis of the tricyclic 6-6-6 and 6-7-6 ring systems of the abietane- and icetexane-type diterpenoids from a common intermediate is presented, using alkylation and acid-catalyzed cyclization as key steps. A short synthesis of the tricyclic 6-6-6 and 6-7-6 ring systems of the abietane- and icetexane-type diterpenoids from a common intermediate is presented, using alkylation and acid-catalyzed cyclization as key steps.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第7期774-776,共3页 中国化学快报(英文版)
基金 the financial support provided by the National Science Foundation of China(No.30873147)
关键词 Abietanes Icetexanes ALKYLATION CYCLIZATION Abietanes Icetexanes Alkylation Cyclization
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参考文献13

  • 1E.M. Simmons, R. Sarpong, Nat. Prod. Rep. 26 (2009) 1195.
  • 2Y. Suto, K. Kaneko, N. Yamagiwa, et al. Tetrahedron Lett. 51 (2010) 6329.
  • 3N.W. Jan, H.J. Liu, M.T. Hsieh, et al. Eur. J. Org. Chem. 2010 (2010) 4271.
  • 4A. Carita, A.C.B, Burtoloso, Tetrahedron Lett. 51 (2010) 686.
  • 5F. de, J. Cortez, R. Sarpong, Org. Lett. 12 (2010) 1428.
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  • 7C.E. Hartmann, P.J. Gross, M. Niegerb, et al. Org. Biomol. Chem. 7 (2009) 5059.
  • 8Compound 9: colorless needle crystals, nap 99-100 ℃, IR (KBr): 2929, 1595, 1488, 1463, 1319, 1080 cm-1.
  • 9IH NMR (400 MHz, CDCI3): 81.62-1.68 (m, 4H), 1.96 (t, 2H, J = 8.0 Hz), 2.19 (s, 2H), 2.53 (s, 2H), 2.66 (t, 2H, J = 7.6 Hz), 3.72 (s, 3H), 3.78 (s, 3H), 3.86 (s, 3H), 6.38 (s,3H).
  • 1013C NMR (100 MHz, CDC13): 3 22.01 (CH2), 22.95 (CH2), 23.97 (CH2), 28.40 (CH2), 31.26 (CH2), 55.79 (CH3), 56.23 (CH3), 60.58 (CH3),119.73 (CH), 127.28 (C), 132.23 (C), 133.07 (C), 139.50 (C), 150.93 (C), 152.72 (C). HR-ESIMS: m/z: C17H2303 [M+H]+ 275.1637 (calcd. 275.1647).

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