Absolute configuration of insect-produced epilachnene

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2787-2790

  Farmer, Jay J ^a   Attygalle, Athula B ^a   Smedley, Scott R ^b   Eisner, Thomas ^b   Meinwald, Jerrold ^a  

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

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DERIVATIZATION; DRUG ISOLATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; IN VITRO STUDY; INSECT; NONHUMAN;

EID: 0343196694     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00490-5     Document Type: Article

References (13)

1. Attygalle, A. B.; McCormick, K. D.; Blankespoor, C. L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. 1993, 90, 5204-5208.
2. Attygalle, A. B.; Blankespoor, C. L.; Eisner, T.; Meinwald, J. Proc. Natl. Acad. Sci. 1994, 91, 12790-12793.
3. Rao, A. V. R.; Rao, B. V.; Bhanu, M. N.; Kumar, V. S. Tetrahedron Lett. 1994, 35, 3201-3204.
4. Rao, B. V.; Kumar, V. S. Tetrahedron Lett., 1995, 36, 147-150.
5. Rao, A. V. R.; Rao, B. V.; Kumar, V. S.; Nagarajan, M.; Sitaramaiah, D. Tetrahedron Lett. 1996, 37, 8613-8616.
6. King, A. G.; Meinwald, J.; Eisner, T.; Blankespoor, C. L. Tetrahedron Lett. 1996, 37, 2141-2144.
7. Gribble, G. W.; Silva, R. A. Tetrahedron Lett. 1996, 37, 2145-2148.
8. For recent reviews of the remarkably diverse defensive chemistry of coccinellid beetles, see: King, A. G.; Meinwald, J. J. Chem. Rev. 1996, 96, 1105-1122 and Daloze, D.; Braekman, J. C.; Pasteels, J. M. Chemoecology, 1995, 173-183.
9. For recent reviews of the remarkably diverse defensive chemistry of coccinellid beetles, see: King, A. G.; Meinwald, J. J. Chem. Rev. 1996, 96, 1105-1122 and Daloze, D.; Braekman, J. C.; Pasteels, J. M. Chemoecology, 1995, 173-183.
10. All key intermediates were characterized on the basis of NMR and MS data. The details of this synthesis are now being prepared for publication.
11. 3P=CHCOPh) are well known, see: Hon, S. H.; Lu, L.; Tetrahedron, 1995, 29, 7937-7942, and refrences cited therein. To our knowledge, the reaction of an ozonide with an unstabilized Wittig reagent to give a non-conjugated product has not been previously reported.
12. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549. This paper is no. 144 in the series Defensive Mechanisms of Arthropods; paper no. 143 is: Blankespoor, C. L.; Paptas, P. W.; Eisner, T. Parasitology, in press.
13. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549. This paper is no. 144 in the series Defensive Mechanisms of Arthropods; paper no. 143 is: Blankespoor, C. L.; Paptas, P. W.; Eisner, T. Parasitology, in press.