Synthesis 2003(13): 1995-2000
DOI: 10.1055/s-2003-41042
PAPER
© Georg Thieme Verlag Stuttgart · New York

Molecular Diversity of Tonghaosu: Synthesis of Lactam-Containing Tonghaosu Analogs

Biao-Lin Yin, Zheng-Min Yang, Tai-Shan Hu, Yu-Lin Wu*
State Key Laboratory of Bio-organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China
e-Mail: ylwu@mail.sioc.ac.cn;
Further Information

Publication History

Received 13 May 2003
Publication Date:
28 August 2003 (online)

Abstract

A new type of tonghaosu analogs containing spiroketal and lactam functionality was synthesized from methyl 2-furoate and amino alcohols. The stereoselective control of spiroketal chirality was also explored.

    References

  • 1 Partial result has been published: Wu Z.-H. Wang J. Li J.-C. Xu Y.-Z. Yu A.-L. Feng Z.-R. Shen J. Wu Y.-L. Guo P.-F. Wang Y.-N. Nat. Prod. R & D [China]  1994,  6:  1 ; Chem. Abstr. 121, 101920
  • 2a Hegnauer R. In Chemotaxonomie der Pflanzen   Vol. 3:  Birkhauser Verlag; Basel: 1964.  p.447 
  • 2b Bohlmann F. Burkhardt T. Zdero C. Naturally Occurring Acetylenes   Academic Press; London: 1973. 
  • 2c Greger H. In The Biology and Chemistry of Compositae   Heywood VH. Harborne JB. Turner BL. Academic Press; London: 1977.  Chap. 32.
  • 2d Bohlmann F. In Chemistry and Biology of Naturally Occurring Acetylenes and Related Compounds   Lam J. Bretler H. Anason T. Hansen L. Elsvier; Amsterdam: 1988.  p.1 
  • 2e Zdero C. Bohlmann F. Plant Syst. Evol.  1990,  171:  1 
  • 3a Bohlmann F. Jastrow H. Ertringshausen G. Kramer D. Chem. Ber.  1964,  97:  801 
  • 3b Bohlmann F. Florentz G. Chem. Ber.  1966,  99:  990 
  • 4a Gao Y. Wu W.-L. Ye B. Zhou R. Wu Y.-L. Tetrahedron Lett.  1996,  37:  893 
  • 4b Gao Y. Wu W.-L. Wu Y.-L. Ye B. Zhou R. Tetrahedron  1998,  54:  12523 
  • 5a Fan J.-F. Zhang Y.-F. Wu Y. Wu Y.-L. Chinese J. Chem.  2001,  19:  1254 ; Chem. Abstr. 136, 263012
  • 5b Fan J.-F. Yin B.-L. Zhang Y.-F. Wu Y.-L. Wu Y. Huaxue Xuebao  2001,  59:  1756 ; Chem. Abstr. 136, 083647
  • 6 Blanchette JA. Brown EV. J. Am. Chem. Soc.  1952,  74:  2098 
  • 7 Fan J.-F. Ph. D. Thesis   Shanghai Institute of Organic Chemistry; China: 2000. 
  • 8 Yin B.-L. Fan J.-F. Gao Y. Wu Y.-L. Synlett  2003,  399 
  • Reviews:
  • 9a Brimble MA. Fares FA. Tetrahedron  1999,  55:  7661 
  • 9b Mead KT. Brewer BN. Curr. Org. Chem.  2003,  7:  227 ; and references cited therein