Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6625-6628

  Schröder, Frank C ^a   Farmer, Jay J ^a   Smedley, Scott R ^b   Eisner, Thomas ^c   Meinwald, Jerrold ^a  

^a Department of Molecular Biology and Genetics   (United States)

^b TRINITY COLLEGE   (United States)

^c Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; MACROLIDE; POLYAMINE DERIVATIVE;

ARTICLE; BEETLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; INSECT; OLIGOMERIZATION;

COCCINELLIDAE; COLEOPTERA; EPILACHNA BOREALIS; INSECTA;

EID: 0032505209     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01404-X     Document Type: Article

References (10)

1. 1. Schröder, F. C.; Farmer, J. J.; Attygalle, A. B.; Smedley, S. R.; Eisner, T.; Meinwald, J. Science 1998, in press.
2. 2. For recent reviews of the diverse defensive chemistry of coccinellid beetles, see: Daloze, D.; Braekman, J.-C.; Pasteels, J. M. Chemoecology 1995, 5/6, 173-183; King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105-1122.
3. 2. For recent reviews of the diverse defensive chemistry of coccinellid beetles, see: Daloze, D.; Braekman, J.-C.; Pasteels, J. M. Chemoecology 1995, 5/6, 173-183; King, A. G.; Meinwald, J. Chem. Rev. 1996, 96, 1105-1122.
4. 3. The pupal secretion of E. borealis contains trace amounts of cyclic oligomers consisting of up to 20 apparently randomly selected units of 7, 8, and 9.
5. 4. Pure (11R)-11-(2-hydroxyethylamino)undecanoic acid (9) can be synthesized more conveniently via a slightly different route as described in reference 1.
6. 5. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399-400.
7. 6. Mukaiyama, T.; Narasaka, K.; Kikuchi, K. Chem. Lett. 1977, 441.
8. 7. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
9. 8. Farmer, J. J.; Attygalle, A. B.; Smedley, S. R.; Eisner, T.; Meinwald, J. Tetrahedron Lett. 1997, 38, 2787-2790.
10. 3 solution, the organic layer was separated and evaporated. The residue was derivatized as described in reference 7.