Total synthesis and stereochemistry assignment of 15-membered peptide alkaloids abyssenine B and mucronine E

Tetrahedron Letters

Volumn 48, Issue 38, 2007, Pages 6717-6721

  Wang, Jing ^a   Schaeffler, Lutz ^a   He, Gang ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ABYSSENINE B; ALDEHYDE; ALKALOID; AMIDE; COPPER DERIVATIVE; DIMETHYLGLYCINE; IODIDE; MUCRONINE E; NATURAL PRODUCT; PHENYLALANINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OLEFINATION; STEREOCHEMISTRY;

EID: 34548033286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.142     Document Type: Article

References (31)

1. Tschesche R., Tobias S., Zerbes R., Radloff M., Kaußmann E.U., and Eckhardt G. Liebigs Ann. Chem. (1974) 1915
2. Fehlhaber H.-W., Uhlendorf J., David S.T., and Tschesche R. Liebigs Ann. Chem. 759 (1972) 195
3. For reviews, see:. Joullié M.M., and Richard D.J. Chem. Commun. (2004) 2011
4. Gournelis D.C., Laskaris G.G., and Verpoorte R. Nat. Prod. Rep. (1997) 75
5. Schmidt U., Lieberknecht A., Griesser H., and Häusler J. Angew. Chem., Int. Ed. Engl. 20 (1981) 281
6. Schmidt U., Lieberknecht A., and Griesser H. Angew. Chem., Int. Ed. Engl. 20 (1981) 1026
7. Schmidt U., Zäh M., and Lieberknecht A. J. Chem. Soc., Chem. Commun. (1991) 1002
8. Heffner R.J., Jiang J., and Joullié M.M. J. Am. Chem. Soc. 114 (1992) 10181
9. East S.P., and Joullié M.M. Tetrahedron Lett. 39 (1998) 7211
10. East S.P., Shao F., Williams L., and Joullié M.M. Tetrahedron 54 (1998) 13371
11. Lipshutz B.H., Huff B.E., McCarthy K.E., Mukarram S.M.J., Siahaan T.J., Vaccaro W.D., Webb H., Falick A.M., and Miller T.A. J. Am. Chem. Soc. 112 (1990) 7032
12. Zhu J., Lai{dotless}̈b T., Chastanet J., and Beugelmans R. Angew. Chem., Int. Ed. 35 (1996) 2517
13. Laïb T., Bois-Choussy M., and Zhu J. Tetrahedron Lett. 41 (2000) 7645
14. Temal-Laíb T., Chastanet J., and Zhu J. J. Am. Chem. Soc. 124 (2002) 583
15. Cristau P., Temal-Laíb T., Bois-Choussy M., Martin M.-T., Vors J.-P., and Zhu J. Chem. Eur. J. 11 (2005) 2668
16. Kim Y.-A., Shin H.-N., Park M.-S., Cho S.-H., and Han S.-Y. Tetrahedron Lett. 44 (2003) 2557
17. Toumi M., Couty F., and Evano G. Angew. Chem., Int. Ed. 46 (2007) 572
18. He G., Wang J., and Ma D. Org. Lett. 9 (2007) 1367
19. Schmidt U., and Schanbacher U. Angew. Chem., Int. Ed. Engl. 22 (1983) 152
20. Pan X., Cai Q., and Ma D. Org. Lett. 6 (2004) 1809
21. For related studies from other groups, see:. Shen R., Lin C.T., Bowman E.J., Bowman B.J., and Porco Jr. J.A. J. Am. Chem. Soc. 125 (2003) 7889
22. Jiang L., Job G.E., Klapars A., and Buchwald S.L. Org. Lett. 5 (2003) 3667
23. Han C., Shen R., Su S., and Porco Jr. J.A. Org. Lett. 6 (2004) 27
24. Coleman R.S., and Liu P.-H. Org. Lett. 6 (2004) 577
25. Hu T., and Li C. Org. Lett. 7 (2005) 2035
26. Stork G., and Zhao K. Tetrahedron Lett. 30 (1989) 2173
27. Chakraborty T.K., Hussain K.A., and Reddy G.V. Tetrahedron 51 (1995) 9179
28. Ma D., Tang G., and Kozikowski A.P. Org. Lett. 4 (2002) 2377
29. Scarpati M.L., Bianco A., Mascitell L., and Passacantilli P. Synth. Commun. 20 (1990) 2565
30. Cai Q., He G., and Ma D. J. Org. Chem. 71 (2006) 5268
31. Hara H., Inoue T., Endoh M., Nakamura H., Takahashi H., and Hoshino O. Heterocycles 42 (1996) 445