Synthesis 2020; 52(05): 735-743
DOI: 10.1055/s-0039-1691494
paper
© Georg Thieme Verlag Stuttgart · New York

Studies towards the Total Synthesis of Kadcotrione B

Julakanti Satyanarayana Reddy
a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India   Email: sjsnreddy@gmail.com
,
Marri Gangababu
a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India   Email: sjsnreddy@gmail.com
,
Patel Manimala
a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India   Email: sjsnreddy@gmail.com
,
Aluru Rammohan
a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India   Email: sjsnreddy@gmail.com
b   Department of Chemistry, Sri Venkateswara University, Tirupati 517502, Andhra Pradesh, India
,
Jillu Singh Yadav
a   Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India   Email: sjsnreddy@gmail.com
› Author Affiliations
Further Information

Publication History

Received: 08 September 2019

Accepted after revision: 05 November 2019

Publication Date:
21 November 2019 (online)


Abstract

A convergent and efficient approach towards the total synthesis of Kadcotrione B is described. For this purpose, the syntheses of two fragments, 6/6/5-fused tricyclic ring and C-9 side chain, were accomplished. The salient features of these syntheses are the utilization of aldol condensation, Evans aldol reaction, Horner–Wadsworth–Emmons olefination, Michael addition, Robinson annulation, and Wacker oxidation.

Supporting Information

 
  • References

  • 1 New address: J. Satyanarayana Reddy, National Health Research Institute, 37 Keyan Road, Zhunan, Miaoli Country, 35053 Taiwan.
  • 2 Liang CQ, Shi YM, Li XY, Luo RH, Li Y, Zheng YT, Sun HD. J. Nat. Prod. 2013; 76: 2350
    • 3a Law YY. Flora Repubulicae Popularis Sinicae, Vol. 30. Science Press; Beijing: 1996: 231-273
    • 3b Xiao WL, Li RT, Huang SX, Pu JX, Sun HD. Nat. Prod. Rep. 2008; 25: 871
    • 3c Shi YM, Xiao WL, Pu JX, Sun HD. Nat. Prod. Rep. 2015; 32: 367
    • 4a Hancke JL, Burgos RA, Ahumada F. Fitoterapia 1999; 70: 451
    • 4b Pharmacopoeia of the Peoples Republic of China, Vol. 1. China Chemical Industry Press; Beijing: 2005: 44-45
    • 4c Pharmacopoeia of the Peoples Republic of China, Vol. 1. China Chemical Industry Press; Beijing: 2005: 169
    • 4d Panossian A, Wikman G. J. Ethnopharmacol. 2008; 118: 183 
    • 5a Song WZ, Xiao PG. Chin. Trad. Herb. Drugs 1982; 13: 40
    • 5b Opletal L, Sovova H, Bartlova M. J. Chromatogr. B 2004; 812: 357
    • 7a Chen DF, Zhang SX, Wang HK, Zhang SY, Sun QZ, Cosentino LM, Lee KH. J. Nat. Prod. 1999; 62: 94
    • 7b Sun HD, Qiu SX, Lin LZ, Wang ZY, Lin ZW, Pengsuparp T, Pezzuto JM, Pong HH. S, Cordell CA, Farnsworth NR. J. Nat. Prod. 1996; 59: 525
    • 8a Zhang Y. Liquor Making 2006; 33: 108
    • 8b Chen YJ, Li YJ, Lu SG. J. Northeast. Agric. Univ. 1998; 29: 195
    • 8c Zhao JH, Li AM, Zhang FL, Wang YF, Wang YP. Special Wild Econ. Anim. Plant. Res. 1998; 3: 20
    • 8d Li JY, Hu YJ. J. Hebei Forestry College 1994; 19: 288
    • 8e Sun CB, Wang S, Ding XY, Li ZX. Food Machinery 2003; 6: 9
    • 9a Luo X, Shi YM, Luo RH, Luo SH, Li XN, Wang RR, Li SH, Zheng YT, Du X, Xiao WL, Pu JX. Org. Lett. 2012; 14: 1286
    • 9b Xue YB, Yang JH, Li XN, Du X, Pu JX, Xiao WL, Su J, Zhao W, Li Y, Sun HD. Org. Lett. 2011; 13: 1564
    • 9c Meng FY, Sun JX, Li X, Yu HY, Li SM, Ruan HL. Org. Lett. 2011; 13: 1502
    • 9d Lin YC, Lo IW, Chen SY, Lin PH, Chien CT, Chang SY, Shen YC. Org. Lett. 2011; 13: 446
    • 9e Cheng YB, Liao TC, Lo IW, Chen YC, Kuo YC, Chen SY, Chien CT, Shen YC. Org. Lett. 2010; 12: 1016
    • 10a Reddy JS, Manimala P, Gangababu M, Rammohan A, Yadav JS. ChemistrySelect 2019; 4: 5345
    • 10b Yadav JS, Amrutapu SK, Pabbaraja S. ChemistrySelect 2017; 2: 1850
    • 10c Mohapatra DK, Reddy DS, Mallampudi NA, Yadav JS. Eur. J. Org. Chem. 2014; 5023
    • 10d Yadav JS, Singh VK, Srihari P. Org. Lett. 2014; 16: 836
    • 10e Yadav JS, Goreti R, Pabbaraja S, Sridhar B. Org. Lett. 2013; 15: 3782
    • 10f Yadav JS, Das S, Reddy JS, Thrimurtulu N, Prasad AR. Tetrahedron Lett. 2010; 51: 4050
    • 11a Hagiwara H, Uda H. J. Org. Chem. 1988; 53: 2308
    • 11b Nozawa M, Akita T, Hoshi T, Suzuki T, Hagiwara H. Synlett 2007; 661
    • 11c Ling T, Poupon E, Rueden JE, Kim HS, Theodorakis AE. J. Am. Chem. Soc. 2002; 124: 12263
    • 11d Allemann C, Gordillo R, Clemente FR, Cheong PH.-Y, Houk KN. Acc. Chem. Res. 2004; 37: 558
    • 11e Scheck M, Koch MA, Waldman H. Tetrahedron 2008; 64: 4792
    • 11f Dhiman S, Ramasastry SS. V. Org. Lett. 2015; 17: 5116
  • 12 Escher S, Giersch W, Ohloff G. Helv. Chem. Acta 1981; 64: 943
  • 13 Assefa H, Nimrod A, Walker L, Sindelar R. Bioorg. Med. Chem. Lett. 2001; 11: 1619
  • 14 Smith AB, Mewshaw R. J. Org. Chem. 1984; 49: 3685
    • 16a Mehta G, Shinde HM. J. Org. Chem. 2012; 77: 8056
    • 16b Benerjee AK, Laya-Memo M. Stud. Nat. Prod. Chem. 2000; 24: 175
  • 17 The relative configuration was determined by X-ray crystallographic analysis. CCDC 1942076 (3) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
    • 18a Mulzer J, Mantoulidis A, Ohler E. Tetrahedron Lett. 1998; 39: 8633
    • 18b Wang G, Yin N, Negishi EI. Chem. Eur. J. 2011; 17: 4118
    • 19a Rubsam F, Evers AM, Michel C, Giannis A. Tetrahedron Lett. 1997; 53: 1707
    • 19b Still WC, Gennari C. Tetrahedron Lett. 1983; 24: 4405
  • 20 Seifert A, Vomund S, Grohmann K, Kriening S, Urlacher VB, Laschat S, Pleiss J. ChemBioChem 2009; 10: 853
    • 21a Bal BS, Childers WE. Jr, Pinnick HW. Tetrahedron 1981; 37: 2091
    • 21b Kraus GA, Roth B. J. Org. Chem. 1980; 45: 4825
    • 22a Sudhakar G, Reddy KJ, Nanubolu JB. Tetrahedron 2013; 69: 2419
    • 22b Evans DA, Ennis MD, Mathre DJ. J. Am. Chem. Soc. 1982; 104: 1737
    • 22c Brukner S, Weise M, Schobert R. J. Org. Chem. 2018; 83: 10805
    • 22d Burkhardt I, Dickschat JS. Eur. J. Org. Chem. 2018; 3144
    • 23a Fuwa H, Nakajima M, Shi J, Takeda Y, Saito T, Sasaki M. Org. Lett. 2011; 13: 1106
    • 23b Yokoe H, Sasaki H, Yoshimura T, Shindo M, Yoshida M, Shishido K. Org. Lett. 2007; 9: 969
    • 23c Suzuki T, Fuzimura M, Fujita K, Kobayashi S. Tetrahedron 2017; 73: 3652
    • 24a Tamai Y, Hagiwara H, Uda H. J. Chem. Soc., Perkin Trans. 1 1986; 1311
    • 24b Houbrechts Y, Laszlo P, Pennetreau P. Tetrahedron Lett. 1986; 27: 705
    • 24c Horton M, Pattenden G. Tetrahedron Lett. 1983; 24: 2125