Stereoselective Heck-Matsuda Arylations of Chiral Dihydrofurans with Arenediazonium Tetrafluoroborates; An Efficient Enantioselective Total Synthesis of (-)-Isoaltholactone

Abstract

The Heck-Matsuda arylation of chiral 2-(S)-hydroxy­methyl dihydrofurans (endocyclic enolethers) and its derivatives, employing arenediazonium tetrafluoroborates, was developed into a highly efficient, practical and diastereoselective synthetic process. This methodology was applied to the total synthesis of the styryllactone (-)-isoaltholactone in seven steps with an overall yield of ˜25%, from the readily available chiral 2-hydroxymethyldihydrofuran. The strategy permits the synthesis of several other aromatic analogues of isoaltholactone.

Heck reaction - palladium - diazonium compounds - catalysis - stereoselectivity

References

For excellent reviews on the chemistry and synthesis of styryllactones, see:

<A NAME="RC01007SS-1A">1a</A> Harris JM. Li M. Scott JG. O’Doherty GA. In Strategies and Tactics in Organic Synthesis   Vol. 5:  Harmata M. Elsevier; Amsterdam: 2004.  p.221 

<A NAME="RC01007SS-1B">1b</A> de Fatima A. Modolo LV. Conegero LS. Pilli RA. Ferreira CV. Khon LK. de Carvalho JE. Curr. Med. Chem.  2006,  13:  3371 

<A NAME="RC01007SS-2A">2a</A> Su Y.-L. Yang C.-S. Teng S.-J. Zhao G. Ding Y. Tetrahedron  2001,  57:  2147 

<A NAME="RC01007SS-2B">2b</A> Mukai C. Hirai S. Hanaoka M. J. Org. Chem.  1997,  62:  6619 

<A NAME="RC01007SS-2C">2c</A> Peris E. Cave A. Estornell E. Zafra-Polo MC. Figadère B. Cortes D. Bermejo A. Tetrahedron  2002,  58:  1335 

<A NAME="RC01007SS-2D">2d</A> Shing TKM. Tsui H.-C. Zhou Z.-H. J. Org. Chem.  1995,  60:  3121 

<A NAME="RC01007SS-2E">2e</A> Pirrung MC. Lee YR. Morehead AT. McPhail A. J. Nat. Prod.  1998,  61:  89 

<A NAME="RC01007SS-2F">2f</A> Surivet J.-P. Vatèle J.-M. Tetrahedron Lett.  1997,  38:  819 

<A NAME="RC01007SS-2G">2g</A> Yoda H. Nakaseko Y. Takabe K. Synlett  2002,  1532 

<A NAME="RC01007SS-2H">2h</A> Tsubuki M. Kanai K. Nagase H. Honda T. Tetrahedron  1999,  55:  2493 

<A NAME="RC01007SS-3">3</A> For an account of the present status of organic synthesis, see: Wilson RM. Danishefsky SJ. J. Org. Chem.  2006,  71:  8329 

<A NAME="RC01007SS-4">4</A> For an excellent review on the use of arenediazonium salts, see: Roglans A. Pla-Quintana A. Moreno-Mañas M. Chem. Rev.  2006,  106:  4622 

<A NAME="RC01007SS-5A">5a</A> Oliveira DF. Severino EA. Correia CRD. Tetrahedron Lett.  1999,  40:  2083 

<A NAME="RC01007SS-5B">5b</A> Carpes MJS. Correia CRD. Tetrahedron Lett.  2002,  43:  741 

<A NAME="RC01007SS-5C">5c</A> García ALL. Correia CRD. Tetrahedron Lett.  2003,  44:  1553 

<A NAME="RC01007SS-5D">5d</A> García ALL. Carpes MJS. de Oca ACBM. dos Santos MAG. Santana CC. Correia CRD. J. Org. Chem.  2005,  70:  1050 

<A NAME="RC01007SS-5E">5e</A> Pastre JC. Correia CRD. Org. Lett.  2006,  8:  1657 

<A NAME="RC01007SS-5F">5f</A> Burtoloso ACB. Garcia ALL. Miranda KC. Correia CRD. Synlett  2006,  3145 

<A NAME="RC01007SS-6">6</A> Severino EA. Costenaro ER. García ALL. Correia CRD. Org. Lett.  2003,  5:  305 

<A NAME="RC01007SS-7A">7a</A> Yadav JS. Krishnam R. Purushothama R. Rajaiah G. Tetrahedron: Asymmetry  2005,  16:  3283 

<A NAME="RC01007SS-7B">7b</A> Yadav JS. Rajaiah G. Raju K. Tetrahedron Lett.  2003,  44:  5831 

<A NAME="RC01007SS-7C">7c</A> Peng X. Li A. Lu J. Wang Q. Pan X. Chan ASC. Tetrahedron  2002,  58:  6799 

<A NAME="RC01007SS-7D">7d</A> Harris JM. OŽDoherty GA. Org. Lett.  2000,  2:  2983 

<A NAME="RC01007SS-7E">7e</A> Harris JM. O’Doherty GA. Tetrahedron  2001,  57:  5161 

<A NAME="RC01007SS-7F">7f</A> Tsubuki M. Kanai K. Nagase H. Honda T. Tetrahedron  1999,  55:  2493 

<A NAME="RC01007SS-7G">7g</A> Shing TKM. Tsui HC. Zhou ZH. J. Org. Chem.  1995,  60:  3121 

<A NAME="RC01007SS-7H">7h</A> Tsubuki M. Kanai K. Honda T. Synlett  1993,  653 

<A NAME="RC01007SS-7I">7i</A> Colegate SM. Din LB. Latiff A. Salleh KM. Samsudin MW. Skelton BW. Tadano K.-I. White AH. Zakaria Z. Phytochemistry  1990,  29:  1701 

<A NAME="RC01007SS-7J">7j</A> Gesson JP. Jacquesy JC. Mondon M. Tetrahedron  1989,  45:  2627 

<A NAME="RC01007SS-7K">7k</A> Gesson JP. Jacquesy JC. Mondon M. Tetrahedron Lett.  1987,  28:  3945 

<A NAME="RC01007SS-8A">8a</A> Ravid U. Silverstein RM. Smith LR. Tetrahedron  1978,  34:  1449 

<A NAME="RC01007SS-8B">8b</A> Takle A. Kocienski P. Tetrahedron  1990,  46:  4503 

<A NAME="RC01007SS-9">9</A>

The endocyclic enolether 12 is a rather volatile compound. Use of reduced pressure should be avoided during its isolation and purification.

<A NAME="RC01007SS-10">10</A>

An interesting alternative to the use of dihydrofuran is the use of a balloon of carbon monoxide. A dark blue solution forms after a few minutes of exposure which stays stable for a long time, without any signs of Pd precipitation. However, upon addition of the remaining reagents, formation of Pd black begins to occur in the reaction medium.

<A NAME="RC01007SS-11">11</A> For a comprehensive review on substrate-directable reactions, see: Hoveyda A. Evans DA. Fu GC. Chem. Rev.  1993,  93:  1307 

<A NAME="RC01007SS-12A">12a</A> Valverde S. Martin-Lomas M. Herradon B. Garcia-Ochoa S. Tetrahedron  1987,  43:  1985 

<A NAME="RC01007SS-12B">12b</A> Tronchet JMJ. Gentile B. Helv. Chim. Acta  1979,  62:  2091 

<A NAME="RC01007SS-13A">13a</A> Ando K. Tetrahedron Lett.  1995,  36:  4105 

<A NAME="RC01007SS-13B">13b</A> Ando K. J. Org. Chem.  1997,  62:  1934 

<A NAME="RC01007SS-13C">13c</A> Ando K. J. Org. Chem.  2000,  65:  4745 

<A NAME="RC01007SS-14">14</A> Armarego WLF. Perrin DD. Purification of Laboratory Chemicals   4th ed.:  Butterworth-Heinemann; Oxford: 1998.