Total synthesis of chaetoquadrins A-C

Organic Letters

Volumn 15, Issue 3, 2013, Pages 658-661

  Kim, U Bin ^a   Furkert, Daniel P ^a   Brimble, Margaret A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; CHAETOQUADRIN A; CHAETOQUADRIN B; CHAETOQUADRIN C; FUSED HETEROCYCLIC RINGS; LACTONE; MONOAMINE OXIDASE INHIBITOR; SPIRO COMPOUND;

ARTICLE; ASCOMYCETES; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ASCOMYCOTA; BIOLOGICAL AGENTS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; LACTONES; MOLECULAR STRUCTURE; MONOAMINE OXIDASE INHIBITORS; SPIRO COMPOUNDS;

EID: 84873390594     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303482k     Document Type: Article

References (17)

1. Fujimoto, H.; Nozawa, M.; Okuyama, E.; Ishibashi, M. Chem. Pharm. Bull. 2002, 50, 330-336
2. Li, M. L.; Zou, Q.; Li, G. Y. Chin. Chem. Lett. 2010, 21, 1203-1205
3. For selected examples, see: Yuen, T.-Y.; Brimble, M. A. Org. Lett. 2012, 14, 5154-5157 and references within
4. Bruder, M.; Haseler, P. L.; Muscarella, M.; Lewis, W.; Moody, C. J. J. Org. Chem. 2009, 75, 353-358
5. Czepa, A.; Hofmann, T. J. Agric. Food Chem. 2003, 51, 3865-3873
6. Chromenes, chromanones, and chromones; Ellis, G. P., Ed.; Wiley: New York, 1977; Chapter 8, pp 698-699.
7. Levison, J. J.; Robinson, S. D. Inorg. Phys. Theor. 1970, 2947-2954
8. Yue, C. J; Liu, Y.; He, R. J. Mol. Catal. A 2006, 259, 17-23
9. There are surprisingly few general asymmetric approaches to α-chiral β-arylated compounds. For examples, see: Molander, G. A.; Shin, I.; Jean-Gérard, L. Org. Lett. 2010, 12, 4384-4387 and references within
10. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737-1739
11. Fresno, N.; Perez-Fernandez, R.; Goya, P.; Jimeno, M.; Alkorta, I.; Elguero, J.; Menendez-Taboada, L.; García-Granda, S. Tetrahedron 2011, 67, 9104-9111
12. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496-6511
13. Myers, A. G.; Bryant, H. Y. Org. Synth. 2000, 77, 22-28
14. Stang, E. M.; White, M. C. Nat. Chem. 2009, 1, 547-551
15. Aldehyde 19 was prepared in two steps from ethyl (S)-3-hydroxybutyrate via known procedures. See: Fernandes, R. A.; Mulay, S. V. J. Org. Chem. 2010, 75, 7029-7032
16. Cergol, K. M.; Coster, M. J. Nat. Protoc. 2007, 2, 2568-2573
17. Aldehyde 21 was prepared in two steps from ethyl (R)-3-hydroxybutyrate via known procedures. See: Fernandes, R. A.; Mulay, S. V. J. Org. Chem. 2010, 75, 7029-7032