Total synthesis of arenamide A and its diastereomer

Tetrahedron Letters

Volumn 50, Issue 49, 2009, Pages 6851-6854

  Chandrasekhar, S ^a   Pavankumarreddy, G ^a   Sathish, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ARENAMIDE A; DEPSIPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; DIASTEREOISOMER; EPOXIDATION; MACROLACTONIZATION; ONE POT SYNTHESIS;

EID: 70350026684     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.119     Document Type: Article

References (15)

1. Blunt J.W., Copp B.R., Hu W.P., Munro M.H.G., Northcote P.T., and Prinsep M.R. Nat. Prod. Rep. 26 (2009) 170-244
2. Asolkar R.N., Freel K.C., Jensen P.R., Fenical W., Kondratyuk T.P., Park E.J., and Pezzuto J.M. J. Nat. Prod. 72 (2009) 396-402
3. Chandrasekhar S., Rao C.L., Seenaiah M., Naresh P., Jagadeesh B., Manjeera D., Sarkar A., and Bhadra M.P. J. Org. Chem. 74 (2009) 401-404
4. Fenical et al. confirmed the configuration in arenamide A at C-28 and C-29 (28R,29R) as mentioned in the text, but according to the structure shown in the graphical abstract the configuration was (28S,29S). Due to this ambiguity we synthesized both isomers of Arenamide A (1 and 2), see Ref. 2.
5. Sawant K.B., Ding F., and Jennings M.P. Tetrahedron Lett. 48 (2007) 5177-5180
6. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974-5976
7. Hiscock S.D., Hitchcock P.B., and Parsons P.J. Tetrahedron 54 (1998) 11567-11580
8. Mori K. Tetrahedron 37 (1981) 1341-1342
9. Liu H.-J., Yip J., and Shia K.-S. Tetrahedron Lett. 38 (1997) 2253-2256
10. Epp J.B., and Widlanski T.S. J. Org. Chem. 64 (1999) 293-295
11. Nicolaou K.C., and Webber S.E. Synthesis (1986) 453-461
12. + = 225.
13. + = 360.1781, found: 360.1788.
14. + = 672.4331, found: 672.4336.
15. + = 672.4331, found: 672.4336.