Citation: De-Lin Chen, Feng-Peng Wang, Xiao-Yu Liu. A convergent approach to the tetracyclic core of atisane diterpenes[J]. Chinese Chemical Letters, ;2016, 27(01): 59-62. doi: 10.1016/j.cclet.2015.09.005 shu

A convergent approach to the tetracyclic core of atisane diterpenes

  • Corresponding author: Feng-Peng Wang,  Xiao-Yu Liu, 
  • Received Date: 13 April 2015
    Available Online: 9 May 2015

    Fund Project: This research was supported by the National Natural Science Foundation of China(No. 81273387). (No. 81273387)

  • Atisane diterpenes are biologically interesting natural products. We report here a convergent approach to construct the tetracyclic core of the atisane skeleton. The two segments were assembled through a Wittig reaction, while an intramolecular Aldol condensation served as the key step to furnish the tetracyclic skeleton.
  • 加载中
    1. [1]

      [1] J.D. Connolly, R.A. Hill, Dictionary of Terpenoids, 1st. ed, Chapman and Hall, London, 1991.

    2. [2]

      [2] J.R. Hanson, Diterpenoids, Nat. Prod. Rep. 17(2000) 165-174.

    3. [3]

      [3] L.A. Mitscher, G.S.R. Rao, T. Veysoglu, S. Drake, T. Haas, Isolation and identification of trachyloban-19-oic and(-)-kaur-16-en-19-oic acids as antimicrobial agents from the prairie sunflower, helianthus annuus, J. Nat. Prod. 46(1983) 745-746.

    4. [4]

      [4] S.Y. Ryu, J.W. Ahn, Y.N. Han, B.H. Han, S.H. Kim, In vitro antitumor activity of diterpenes from Aralia cordata, Arch. Pharm. Res. 19(1996) 77-78.

    5. [5]

      [5] W.M. Daniewski, P. Skibicki, E. Bloszyk, M. Budesinsky, M. Holub, Constituents of Helianthus mollis lam. and their antifeedant activity, Polish J. Chem. 67(1993) 1255-1259.

    6. [6]

      [6] M. Toyota, M. Yokota, M. Ihara, Construction of bicyclo[2.2.2] octane ring system via homoallyl-homoallyl radical rearrangement, Tetrahedron Lett. 40(1999) 1551-1554.

    7. [7]

      [7] M. Ihara, M. Toyota, K. Fukuyama, T. Kametani, Stereocontrolled construction of a spiro fused bicyclo[2.2.2] Octane ring system by the intramolecular double michael reaction, Tetrahedron Lett. 25(1984) 2167-2170.

    8. [8]

      [8] M. Ihara, M. Toyota, K. Fukuyama, T. Kametani, Intramolecular double Michael reaction. Part Ⅱ. Synthesis of isoatisirene type compound, Tetrahedron Lett. 25(1984) 3235-3238.

    9. [9]

      [9] M. Ihara, M. Toyota, K. Fukuyama, T. Kametani, Intramolecular double Michael reaction ⅡI stereoselective chiral synthesis of atisiran-15-one, Tetrahedron Lett. 26(1985) 1537-1540.

    10. [10]

      [10] M. Ihara, M. Toyota, K. Fukuyama, T. Kametani, An enantioselective total synthesis of(+)-atisirene by intramolecular double Michael reaction, J. Chem. Soc. Perkin Trans. 1(1986) 2151-2161.

    11. [11]

      [11] M. Toyota, T. Wada, K. Fukuyama, M. Ihara, Total synthesis of(±)-methyl atis-16-en-19-oate via homoallyl-homoallyl radical rearrangement, J. Am. Chem. Soc. 120(1998) 4916-4925.

    12. [12]

      [12] M. Toyota, T. Wada, M. Ihara, Total syntheses of(-)-methyl atis-16-en-19-oate,(-)-methyl kaur-16-en-19-oate, and(-)-methyl trachyloban-19-oate by a combination of palladium-catalyzed cycloalkenylation and homoallyl-homoallyl radical rearrangement, J. Org. Chem. 65(2000) 4565-4570.

    13. [13]

      [13] E.C. Cherney, J.M. Lopchuk, J.C. Green, P.S. Baran, A unified approach to ent-atisane diterpenes and related alkaloids:synthesis of(-)-methyl atisenoate,(-)-isoatisine, and the hetidine skeleton, J. Am. Chem. Soc. 136(2014) 12592-12595.

    14. [14]

      [14] M. Toyota, M. Yokota, M. Ihara, First total synthesis of(±)-methyl gummiferolate using a homoallyl-homoallyl radical rearrangement reaction, Org. Lett. 1(1999) 1627-1629.

    15. [15]

      [15] M. Toyota, M. Yokota, M. Ihara, Remarkable control of radical cyclization processes of cyclic enyne:total syntheses of(±)-methyl gummiferolate,(±)-methyl 7β-hydroxykaurenoate, and(±)-methyl 7-oxokaurenoate and formal synthesis of(±)-gibberellin A12 from a common synthetic precursor, J. Am. Chem. Soc. 123(2001) 1856-1861.

    16. [16]

      [16] M. Toyota, T. Asano, M. Ihara, Total synthesis of serofendic acids A and B employing tin-free homoallyl-homoallyl radicalrearrangement, Org. Lett.7(2005) 3929-3932.

    17. [17]

      [17] D.L. Chen, F.P. Wang, Efficient synthesis of the C/D rings of atisine-type C20-diterpenoid alkaloids, Chin. Chem. Lett. 23(2012) 1378-1380.

    18. [18]

      [18] F.A.J. Kerdesky, S.P. Schmidt, J.H. Holms, et al., Synthesis and 5-lipoxygenase inhibitory activity of 5-hydroperoxy-68, 11, 14-eicosatetraenoic acid analogs, J. Med. Chem. 30(1987) 1177-1186.

    19. [19]

      [19] K.W. Tsao, B. Devendar, C.C. Liao, Ring rearrangement metathesis of 2-allylbicyclo[2.2.2] octenes:a short entry to cis-hydrindenols from 2-methoxyphenols, Tetrahedron Lett. 54(2013) 3055-3059.

    20. [20]

      [20] V. Van Rheenen, Copper-catalyzed oxygenation of branched aldehydes-an efficient ketone synthesis, Tetrahedron Lett. 10(1969) 985-988.

    21. [21]

      [21] J.A. Zallkowski, K.E. Gilbert, W.T. Borden, Oxidation of 7-(hydroxymethyl)bicyclo[3.3.1] nonan-3-ol. Convenient synthesis of bicyclo[3.3.1] nonane-3, 7-dione, J. Org. Chem. 45(1980) 346-347.

    22. [22]

      [22] H.N. Sun, C. Yang, F. Gao, Z. Li, W.J. Xia, Oxidative C-C bond cleavage of aldehydes via visible-light photoredox catalysis, Org. Lett. 15(2013) 624-627.

  • 加载中
    1. [1]

      Kuan DengFei YangZhi-Qi ChengBi-Wen RenHua LiuJiao ChenMeng-Yao SheLe YuXiao-Gang LiuHai-Tao FengJian-Li Li . Construction of wavelength-tunable DSE quinoline salt derivatives by regulating the hybridization form of the nitrogen atom and intramolecular torsion angle. Chinese Chemical Letters, 2024, 35(10): 109464-. doi: 10.1016/j.cclet.2023.109464

    2. [2]

      Yuting Zhang Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037

    3. [3]

      Yukun Chang Haoqin Huang Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095

Metrics
  • PDF Downloads(0)
  • Abstract views(686)
  • HTML views(5)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return