A Versatile Access to Enantiomerically Pure 5-Substituted 4-Hydroxy­cyclohex-2-enones: An Advanced Hemisecalonic Acid A Model

Abstract

A convenient route for the versatile preparation of 5-substituted 4-hydroxycyclohex-2-enones via the addition of an organocuprate to a cyclohex-2-enone is reported. These compounds are important intermediates in our synthetic studies towards the myco­toxin secalonic acid A.

stereoselective synthesis - cyclohexenone - Michael addition­ - domino reaction - natural products

References

<A NAME="RT03407SS-1A">1a</A> Minio Y. Yunio M. Komei M. Chem. Pharm. Bull.  1971,  19:  199 

<A NAME="RT03407SS-1B">1b</A> Kraft F. Arch. Pharm. (Weinheim, Ger.)  1906,  244:  336 

<A NAME="RT03407SS-1C">1c</A> Jacobi C. Arch. Pharm. (Weinheim, Ger.)  1897,  39:  104 

<A NAME="RT03407SS-1D">1d</A> Hale ME. Bryologist  1958,  61:  81 

<A NAME="RT03407SS-1E">1e</A> Andersen R. Büchi G. Kobbe B. Demain AL. J. Org. Chem.  1977,  42:  352 

<A NAME="RT03407SS-1F">1f</A> Howard CC. Johnstone RAW. Entwistle ID. J. Chem. Soc., Chem. Commun.  1973,  464 

<A NAME="RT03407SS-1G">1g</A> Howard CC. Johnstone RAW. J. Chem. Soc., Perkin Trans. 1  1973,  2440 

<A NAME="RT03407SS-1H">1h</A> Franck B. Thiele OW. Reschke T. Angew. Chem.  1961,  73:  494 

<A NAME="RT03407SS-1I">1i</A> Franck B. Thiele OW. Reschke T. Chem. Ber.  1962,  95:  1328 

<A NAME="RT03407SS-2">2</A> Lesch B. Bräse S. Angew. Chem. Int. Ed.  2004,  43:  115 ; Angew. Chem. 2004, 116, 118

<A NAME="RT03407SS-3">3</A> Ohnemüller UK. Nising CF. Nieger M. Bräse S. Eur. J. Org. Chem.  2006,  6:  1535 

<A NAME="RT03407SS-4">4</A> Barros MT. Maycock CD. Ventura MR. J. Org Chem.  1997,  62:  3984 

<A NAME="RT03407SS-5">5</A> Matsuo K. Sugimura W. Shimizu Y. Nishiwaki K. Kuwajima H. Heterocycles  2000,  53:  1505 

<A NAME="RT03407SS-6">6</A> Trost BM. Romero AG. J. Org. Chem.  1986,  51:  2332 

<A NAME="RT03407SS-7">7</A> Audia JE. Boisvert L. Patten AD. Villalobos A. Danishefsky SJ. J. Org. Chem.  1989,  54:  3738 

<A NAME="RT03407SS-8">8</A> Kamenecka TM. Overman LE. Tetrahedron Lett.  1994,  35:  4279 

<A NAME="RT03407SS-9A">9a</A> Krause N. Gerold A. Angew. Chem., Int. Ed. Engl.  1997,  36:  186 ; Angew. Chem. 1997, 109, 194

<A NAME="RT03407SS-9B">9b</A> Knochel P. Singer RD. Chem. Rev.  1993,  93:  2117 

<A NAME="RT03407SS-9C">9c</A> Krause N. Modern Organocopper Chemistry   Wiley-VCH; Weinheim: 2002. 

<A NAME="RT03407SS-10">10</A> Kaburagi Y. Kishi Y. Org. Lett.  2007,  9:  723 

<A NAME="RT03407SS-11">11</A>

Characterization details for this compound are available from the authors.