Synthesis of 4-methyldienoates using a vinylogous Horner-Wadsworth-Emmons reagent. Application to the synthesis of trichostatic acid.

作者: John T. Markiewicz , Douglas J. Schauer , Joakim Löfstedt , Steven J. Corden , Olaf Wiest

DOI: 10.1021/JO902422Y

关键词:

摘要: The utility of the unsaturated phosphonate 1 as a vinylogous Horner−Wadsworth−Emmons reagent was explored in reactions with aldehydes affording 4-methyldienoate esters. Factors that affect E/Z selectivity were studied. A simplified synthesis trichostatic acid 3 accomplished to demonstrate this reagent.

参考文章(45)
Sherry R. Chemler, D.Scott Coffey, William R. Roush, An improved synthesis of the (E,Z)-dienoate precursor of (+)-damavaricin D via a vinylogous Horner-Wadsworth-Emmons reaction Tetrahedron Letters. ,vol. 40, pp. 1269- 1272 ,(1999) , 10.1016/S0040-4039(98)02638-0
Sylvie Mouné,, Gilles Niel, Magali Busquet, Ian Eggleston, Patrick Jouin, TOTAL SYNTHESIS OF DOLATRIENOIC ACID : A SUBUNIT OF DOLASTATIN 14 Journal of Organic Chemistry. ,vol. 62, pp. 3332- 3339 ,(1997) , 10.1021/JO962217A
Joëlle Prunet, Recent Methods for the Synthesis of (E)-Alkene Units in Macrocyclic Natural Products Angewandte Chemie International Edition. ,vol. 42, pp. 2826- 2830 ,(2003) , 10.1002/ANIE.200301628
Peter Brandt, Per-Ola Norrby, Ivar Martin, Tobias Rein, A Quantum Chemical Exploration of the Horner-Wadsworth-Emmons Reaction Journal of Organic Chemistry. ,vol. 63, pp. 1280- 1289 ,(1998) , 10.1021/JO971973T
Narayan S. Chakor, Loana Musso, Sabrina Dallavalle, First total synthesis of cyrmenin B1. Journal of Organic Chemistry. ,vol. 74, pp. 844- 849 ,(2009) , 10.1021/JO802209M
David A. Evans, Scott J. Miller, Michael D. Ennis, Paul L. Ornstein, Asymmetric synthesis of macbecin I Journal of Organic Chemistry. ,vol. 57, pp. 1067- 1069 ,(1992) , 10.1021/JO00030A006