Cafestol to tricalysiolide B and oxidized analogues: Biosynthetic and derivatization studies using non-heme iron catalyst Fe(PDP)

Synlett

Volumn 23, Issue 19, 2012, Pages 2768-2772

  Bigi, Marinus A ^a   Liu, Peng ^b   Zou, Lufeng ^b   Houk, K N ^b   White, M Christina ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

aliphatic; biosynthesis; C H oxidation; cafestol; functionalization; natural product diversification; non heme iron

Indexed keywords

CAFESTOL; CARBON; CYTOCHROME P450; FURAN; HYDROGEN; IRON DERIVATIVE; NONHEME IRON; TERPENE DERIVATIVE; TRICALYSIOLIDE B; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; OXIDATION; PLANT; TRICALYSIA DUBIA;

EID: 84868642021     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0032-1317708     Document Type: Article

References (15)

1. Denisov I. G., Makris T. M., Sligar S. G., Schlichting I. Chem. Rev.: 2005; 105 2253
2. Bruijnincx P. C. A, van Koten G., Gebbink R. J. M. K. Chem. Soc. Rev.: 2008; 37 2716
3. Merkx M., Kopp D. A., Sazinsky M. H., Blazyk J. L., Müller J., Lippard S. J. Angew. Chem. Int. Ed.: 2001; 40 2782
4. Neumann C. S., Fujimori D. G., Walsh C. T. Chemistry & Biology: 2008; 15 99
5. Costas M., Mehn M. P., Jensen M. P., Que L. Jr. Chem. Rev.: 2004; 104 939
6. Okuno T., Ito S., Ohba S., Nishida Y. J. Chem. Soc., dalton Trans.: 1997; 3547
7. Kim C., Chen K., Kim J., Que L. Jr. J. Am. Chem. Soc.: 1997; 119 5964
8. Wu X., Seo M. S., Davis K. M., Lee Y.-M, Chen J., Cho K.-B, Pushkar Y. N., Nam W. J. Am. Chem. Soc.: 2011; 133 20088
9. Bigi J. P., Harman W. H., Lassalle-Kaiser B., Robles D. M., Stich T. A., Yano J., Britt R. D., Chang C. J. J. Am. Chem. Soc.: 2012; 134 1536
10. Groves J. T., Neumann R. J. Org. Chem.: 1988; 53 3891
11. Breslow R., Huang Y., Zhang X., Yang J. Proc. Natl. Acad. Sci. U.S.A.: 1997; 94 11156
12. Das S., Incarvito C. D., Crabtree R. H., Brudvig G. W. Science: 2006; 312 1941
13. Liu W., Groves J. T. J. Am. Chem. Soc.: 2010; 132 12847
14. Liu W., Huang X., Cheng M.-J, Nielsen R. J., Goddard W. A. III, Groves J. T. Science: 2012; 337 1322
15. Paradine S. M., White M. C. J. Am. Chem. Soc.: 2012; 134 2036