Synthesis of Kurasoin B Using
Phase-Transfer-Catalyzed Acylimidazole Alkylation

Michael A. Christiansen; Aaron W. Butler; Amanda R. Hill; Merritt B. Andrus

doi:10.1055/s-0028-1087809

CLUSTER

Synthesis of Kurasoin B Using Phase-Transfer-Catalyzed Acylimidazole Alkylation

Michael A. Christiansen, Aaron W. Butler, Amanda R. Hill, Merritt B. Andrus*
Department of Chemistry and Biochemistry, Brigham Young University, C100 BNSN, Provo, UT 84602, USA
Fax: +1(801)4220153; e-Mail: mbandrus@chem.byu.edu;

Abstract

All articles of this category

Abstract

The hydroxy ketone natural product kurasoin B is synthesized using a phase-transfer-catalyzed alkylation reaction with benzyloxyacetyl imidazole. A biscinchonidinium dimethylnaphthalene catalyst allowed for high yield and near complete selectivity (99% ee) for the S-product using 3-methylbromoindole as the electrophile.

Key words

alkylations - asymmetric catalysis - asymmetric synthesis - natural products - total synthesis

Full Text

References

1 Uchida R. Shiomi K. Inokoshi J. Masuma R. Kawakubo T. Tanaka H. Iwai Y. Omura S. J. Antibiot. 1996, 49: 932

2a Kohl NE. Wilson FR. Mosser SD. Giuliani E. DeSolms SJ. Proc. Natl. Acad. Sci. U.S.A. 1994, 91: 9141

2b Kohl NE. Omer CA. Conner MW. Anthony NJ. Davide JP. Nat. Med. 1995, 1: 792

3a Sunazuka T. Hirose T. Zhi-Ming T. Uchida R. Shiomi K. Harigaya Y. Omura S. J. Antibiotics 1997, 50: 453

3b Hirose T. Sunazuka T. Zhi-Ming T. Handa M. Uchida R. Shiomi K. Harigaya Y. Omura S. Heterocycles 2000, 53: 777

4 Uchida R. Shiomi K. Sunazuka T. Inokoshi J. Nishizawa A. Hirose T. Tanaka H. Iwai Y. Omura S. J. Antibiotics 1996, 49: 886

5a Andrus MB. Hicken EJ. Stephens JS. Org. Lett. 2004, 6: 2289

5b Andrus MB. Hicken EJ. Stephens JC. Bedke DK. J. Org. Chem. 2005, 70: 9470

6 Andrus MB. Hicken EJ. Stephens JC. Bedke DK. J. Org. Chem. 2006, 71: 8651

7 Andrus MB. Christiansen MA. Hicken EJ. Gainer MJ. Bedke KD. Harper KC. Mikkelson SR. Dodson DD. Harris DV. Org. Lett. 2007, 8: 4865

8a Evans DA. Song H.-J. Fandrick KR. Org. Lett. 2006, 8: 3351

8b Evans DA. Fandrick KR. Song H.-J. J. Am. Chem. Soc. 2005, 127: 8942

8c Miyashita A. Suzuki Y. Nagasaki I. Ishiguro C. Iwamoto K.-I. Higashino T. Chem. Pharm. Bull. 1997, 45: 1254

9a O’Donnell MJ. Bennett WD. Wu S. J. Am. Chem. Soc. 1989, 111: 2353

9b Corey EJ. Xu F. Noe MC. J. Am. Chem. Soc. 1997, 119: 12414

9c Lygo B. Wainwright PG. Tetrahedron Lett. 1997, 38: 8595

9d Ooi T. Kameda K. Maruoka K. J. Am. Chem. Soc. 1999, 121: 6519

9e Jew S. Yoo M. Jeong B. Park IY. Park H. Org. Lett. 2002, 4: 4245

9f Park H. Jeong B. Yoo M. Lee J. Park M. Lee Y. Kim M. Jew S. Angew. Chem. Int. Ed. 2002, 41: 3036

9g O’Donnell MJ. Delgado F. Hostettler C. Schwesinger R. Tetrahedron Lett. 1998, 39: 8775

10 Oliveira DJ. Coelho F. Synth. Commun. 2000, 30: 2143

11 Binns MR. Haynes RK. Lambert DE. Schober PA. Turner SG. Aust. J. Chem. 1987, 40: 281

12 Rai-Mali S. Svedrui D. Gazivoda T. Marunovi A. Hergold-Brundi A. Nagl A. Balzarini J. De Clercq E. Mintas M. J. Med. Chem. 2000, 43: 4806

13a Larsen CH. Ridgway BH. Shaw JT. Smith DM. Woerpel KA. J. Am. Chem. Soc. 2005, 127: 10879

13b Hulme AN. Montgomery CH. Tetrahedron Lett. 2003, 44: 7649

13c Okitsu O. Suzuki R. Kobayashi S. J. Org. Chem. 2001, 66: 809

13d Dineen TA. Roush WR. Org. Lett. 2005, 7: 1355

13e Rivkin A. Biswas K. Chou T.-C. Danishefsky SJ. Org. Lett. 2002, 4: 4081

14a Creary X. Geiger CC. J. Am. Chem. Soc. 1982, 104: 4151

14b Hartman M. Christian R. Zbiral E. Liebigs Ann. Chem. 1990, 83

14c Ivonin SP. Lapandin AV. Synth. Commun. 2004, 34: 3727