Synthesis of a ketone analogue of biotin via the intramolecular Pauson-Khand reaction

Organic Letters

Volumn 8, Issue 20, 2006, Pages 4593-4595

  McNeill, Eric ^a   Chen, Irwin ^a   Ting, Alice Y ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOTIN; KETONE;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BIOTIN; KETONES; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 33750055009     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061862t     Document Type: Article

References (14)

1. Chen, I.; Ting, A. Y. Curr. Opin. Biotechnol. 2005, 16, 35 and references therein.
2. Chen, I.; Howarth, M.; Lin, W.; Ting, A. Y. Nat. Methods 2005, 2, 99.
3. Pauson-Khand reaction: (a) Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
4. (b) Pauson, P. L. Tetrahedron 1985, 41, 5855.
5. (c) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. 1998, 37, 911.
6. (d) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 50, 3263.
7. Stumpf, A.; Jeong, N.; Sunghee, H. Synlett 1997, 205.
8. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 3346.
9. Schreiber S. L.; Claus, R. E.; Reagan, J. Tetrahedron Lett. 1982, 23, 3867.
10. Hess, C.; Phillips, R. S. J. Chem. Soc., Perkin Trans. 1 2000, 2821.
11. Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
12. Mukai, C.; Kim, J. S.; Uchiyama, M.; Sakamoto, S.; Hanaoka, M. J. Chem. Soc., Perkin Trans. 1 1998, 2903.
13. (a) Tsuda, T.; Hayashi, T.; Satomi, H.; Kawamoto, T.; Saesuga, T. J. Org. Chem. 1986, 51, 537.
14. (b) Dahnke, K. R.; Paquette, L. A. Organic Syntheses Collection; Wiley: New York, 1998; Vol.9, p 396.