A Concise and Efficient Synthesis of (5R,7S)-Kurzilactone and Its (5S,7R)-Enantiomer by the Mukaiyama Aldol Reaction

Abstract

Natural kurzilactone (5R,7S) and its (5S,7R)-enantiomer were synthesized by a convergent approach using a diastereoselective Mukaiyama aldol reaction to construct the anti diol unit. Finally, a ring-closing metathesis reaction led to the target molecule.

kurzilactone - Mukaiyama reaction - aldol reaction - ring closure - metathesis

References

<A NAME="RZ09209SS-1">1</A> Fu X. Sévenet T. Hamid A. Hadi A. Remy F. Païs M. Phytochemistry  1993,  33:  1272 

<A NAME="RZ09209SS-2">2</A> Jiang B. Chen Z. Tetrahedron: Asymmetry  2001,  12:  2835. 

<A NAME="RZ09209SS-3A">3a</A> Sabitha G. Sudhakar K. Reddy NM. Rajkumar M. Yadav JS. Tetrahedron Lett.  2005,  46:  6567 

<A NAME="RZ09209SS-3B">3b</A> Sabitha G. Narjis F. Swapna R. Yadav JS. Synthesis  2006,  2879 

<A NAME="RZ09209SS-3C">3c</A> Sabitha G. Reddy EV. Yadagiri K. Yadav JS. Synthesis  2006,  3270 

<A NAME="RZ09209SS-3D">3d</A> Sabitha G. Sudhakar K. Yadav JS. Tetrahedron Lett.  2006,  47:  8599 

<A NAME="RZ09209SS-3E">3e</A> Sabitha G. Bhaskar V. Yadav JS. Tetrahedron Lett.  2006,  47:  8179 

<A NAME="RZ09209SS-3F">3f</A> Sabitha G. Swapna R. Reddy EV. Yadav JS. Synthesis  2006,  4242 

<A NAME="RZ09209SS-3G">3g</A> Sabitha G. Sudhakar K. Yadav JS. Synthesis  2007,  705 

<A NAME="RZ09209SS-3H">3h</A> Sabitha G. Bhaskar V. Yadav JS. Synth. Commun.  2008,  38:  1 

<A NAME="RZ09209SS-3I">3i</A> Sabitha G. Bhaskar V. Reddy SS. Yadav JS. Tetrahedron  2008,  64:  10207 

<A NAME="RZ09209SS-3J">3j</A> Sabitha G. Narjis F. Gopal P. Reddy CN. Yadav JS. Tetrahedron: Asymmetry  2009,  20:  184 

<A NAME="RZ09209SS-4">4</A> Schaus S. E. Brandes B. D. Larrow J. F. Tokunaga M. Hansen K. B. Gould A. E. Furrow M. E. Jacobsen E. J. Am. Chem. Soc.  2002,  124:  1307 

<A NAME="RZ09209SS-5">5</A> Kim Y.-J. Tae J. Synlett  2006,  61