Synlett 2015; 26(07): 921-926
DOI: 10.1055/s-0034-1380172
letter
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of Two Pyrrole Spiroketal Alkaloids: Pollenopyrroside A and Capparisine B

Zhi Cao
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
,
Yueqing Li
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
,
Shisheng Wang
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
,
Xiuhan Guo
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
,
Liu Wang
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
,
Weijie Zhao*
School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China   Email: zyzhao@dlut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 25 November 2014

Accepted after revision: 12 January 2015

Publication Date:
10 February 2015 (online)


Abstract

Pollenopyrroside A and capparisine B, two diastereoisomers of pyrrole spiroketal alkaloids isolated from Brassica campestris pollen and Capparis spinosa, were synthesized by an improved microwave-­assisted bishydroxymethylation of pyrrole and acid-catalyzed spirocyclization as key steps with total yields of 2.7 and 8.8%, respectively.

Supporting Information

 
  • References and Notes

    • 1a Tong XG, Zhou LL, Wang YH, Xia C, Wang Y, Liang M, Hou FF, Cheng YX. Org. Lett. 2010; 13: 4478
    • 1b Yang T, Wang Ch, Chou GX, Wu T, Cheng XM, Wang ZT. Food Chem. 2010; 123: 705
    • 1c Guo JL, Feng ZM, Yang YJ, Zhang ZW, Zhang PC. ChemInform 2010; 41: 983
  • 2 Zhao ZF, Zhou LL, Chen X, Cheng YX, Hou FF, Nie J. Chin. Med. J. 2013; 126: 1230
  • 3 Sudhakar G, Kadam VD, Bayya S, Pranitha G, Jagadeesh B. Org. Lett. 2011; 13: 5452
  • 4 Wurst JM, Verano AL, Tan DS. Org. Lett. 2012; 14: 4442
  • 5 Geng HM, Chen JL. Y, Furkert DP, Jiang S, Brimble MA. Synlett 2012; 23: 855
  • 6 Borrero NV, Aponick A. J. Org. Chem. 2012; 77: 8410
  • 7 Teranishi T, Kageyama M, Kuwahara S. Biosci., Biotechnol., Biochem. 2013; 77: 676
  • 8 Geng HM, Stubbing LA, Chen JL, Furkert DP, Brimble MA. Eur. J. Org. Chem. 2014; 6227
  • 9 Huo S, Li Y, Liang C, Liu J, Zhao W. J. Carbohydr. Chem. 2011; 30: 75
  • 10 Taniguchi S, Hasegawa H, Yanagiya S, Tabeta Y, Nakano Y, Takahashi M. Tetrahedron 2001; 57: 2103
  • 11 García Fernández JM, Ortiz Mellet C, Moreno Marín A, Fuentes J. Carbohydr. Res. 1995; 274: 263
  • 12 Benito JM, Rubio E, Gómez-García M, Mellet CO, García Fernández JM. Tetrahedron 2004; 60: 5899
  • 13 Langer V, Micová J, Steiner B, Koós M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2005; 61: o2172
  • 14 Duus J, Gotfredsen CH, Bock K. Chem. Rev. 2000; 100: 4589
    • 15a Azhayev A, Guzaev A, Hovinen J, Mattinen J, Sillanpaa R, Lonnberg H. Synthesis 1994; 396
    • 15b Szarek WA, Rafka RJ, Yang TF, Martin OR. Can. J. Chem. 1995; 73: 1639
    • 15c Praly JP, Bonnevie C, Haung P, Descotes G. Tetrahedron 1996; 52: 9057
  • 16 Fujii N, Otaka A, Sugiyama N, Hatano M, Yajima H. Chem. Pharm. Bull. 1987; 35: 3880
  • 17 Heathcock CH, Ratcliffe R. J. Am. Chem. Soc. 1971; 93: 1746
  • 18 Pallenberg AJ. Tetrahedron Lett. 1992; 33: 7693
  • 19 Horita K, Yoshioka T, Tanaka T, Oikawa Y, Yonemitsu O. Tetrahedron 1986; 42: 3021